Synthesis routes of 1-Chloro-amitriptyline

1-Chloro-amitriptyline

Cat. No. B8430511

M. Wt: 311.8 g/mol

InChI Key: CMGZPJIHOZMOKL-UHFFFAOYSA-N

Attention: For research use only. Not for human or veterinary use.

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Patent

US03991103

Procedure details

1-Chloro-amitriptyline (196 mg) in 3 ml. absolute ethanol was added to an ethanolic solution of 1.1 eq. d-tartaric acid and warmed for 5-10 mins. The title compound was precipitated with ethyl ether as a white powder. After purity and identification checks, the overall yield from amitriptyline base was 32%.

Name

1-Chloro-amitriptyline

Quantity

196 mg

Type

reactant

Reaction Step One

Name

d-tartaric acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

ethanol

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Two

Name

amitriptyline

Identifiers

REACTION_CXSMILES

[CH3:1][N:2]([CH2:4][CH2:5][CH:6]=[C:7]1[C:17]2[CH:18]=[CH:19][CH:20]=[C:21](Cl)[C:16]=2[CH2:15][CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH3:3].C(O)(=O)[C@H]([C@@H](C(O)=O)O)O>C(O)C>[CH3:1][N:2]([CH2:4][CH2:5][CH:6]=[C:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]1=2)[CH3:3]

Inputs

Step One

Name	1-Chloro-amitriptyline
Quantity	196 mg
Type	reactant
Smiles	CN(C)CCC=C1C=2C=CC=CC2CCC3=C1C=CC=C3Cl

Step Two

Name	d-tartaric acid
Quantity	0 (± 1) mol
Type	reactant
Smiles	C([C@@H](O)[C@H](O)C(=O)O)(=O)O

Name	ethanol
Quantity	0 (± 1) mol
Type	solvent
Smiles	C(C)O

Conditions

Other

Conditions are dynamic	1
Details	See reaction.notes.procedure_details.

Workups

TEMPERATURE

Type	TEMPERATURE
Details	warmed for 5-10 mins
Duration	7.5 (± 2.5) min

CUSTOM

Type	CUSTOM
Details	The title compound was precipitated with ethyl ether as a white powder

Outcomes

Product

Name	amitriptyline
Type	product
Smiles	CN(C)CCC=C1C=2C=CC=CC2CCC3=C1C=CC=C3

Source

Open Reaction Database (ORD)

Description

The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.