Ethyl chloroformate → HCID 9892174, compound

HRID 1196454Notes

Reaction equation

HRID 1196454 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.ClC(OCC)=O.[CH3:20][N:21]1[CH2:26][CH2:25][C:24](=[C:27]2[C:33]3[CH:34]=[C:35]([CH2:38][NH2:39])[CH:36]=[CH:37][C:32]=3[CH:31]=[CH:30][C:29]3[CH:40]=[CH:41][CH:42]=[CH:43][C:28]2=3)[CH2:23][CH2:22]1>C(Cl)Cl>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:39][CH2:38][C:35]2[CH:36]=[CH:37][C:32]3[CH:31]=[CH:30][C:29]4[CH:40]=[CH:41][CH:42]=[CH:43][C:28]=4[C:27](=[C:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)[C:33]=3[CH:34]=2)=[O:8])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 15165713HCID 15165713, compound

Product 1

HCID 9892174HCID 9892174, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.6 g (3.2 mmole) of 4-amino-5-chloro-2-methoxybenzoic acid in 15 ml of methylene chloride cooled to -15° C. was added 0.347 g (3.7 mmol) of ethyl chloroformate. The solution was stirred for 30 minutes and 1.0 g (3.2 mmole) of 1-methyl-4-(3-aminomethyl-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine in 10 ml of methylene chloride was added. The solution was allowed to stir at room temperature for 2 hours. The solution was washed with 1N sodium hydroxide solution, water, and brine, and then was dried (MgSO4). After filtration, the solvent was removed under reduced pressure to give 4-amino-5-chloro-2-methoxy-N-((5-(1-methyl-4-piperidinylidene)-5H-dibenzo[a,d]cyclohepten-3-yl)methyl)benzamide as an amorphous foam.

Workup

  1. stirringto stir at room temperature for 2 hours
  2. washThe solution was washed with 1N sodium hydroxide solution, water, and brine
  3. dry with materialwas dried (MgSO4)
  4. filtrationAfter filtration
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5937d396adaa47dbbe02eb3206275411
Source dataset
uspto-grants-1992_05
Patent number
US05114919

Reaction notes

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