Chloroform → HCID 19960831, compound

HRID 53871Notes

Reaction equation

HRID 53871 reaction equation
CS(O)(=O)=O.[CH:6]1([NH:12][C:13]([CH:15]2[CH:23]3[C:18]4([CH:27]=[CH:26][CH:25]=[CH:24][C:19]4=[N:20][CH2:21][CH2:22]3)[S:17][CH2:16]2)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(Cl)(Cl)Cl.[CH2:32]([O:39][C:40](Cl)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(N(CC)CC)C>[CH:6]1([NH:12][C:13]([CH:15]2[CH:23]3[C:18]4([CH:27]=[CH:26][CH:25]=[CH:24][C:19]4=[N:20][CH2:21][CH2:22]3)[S:17][CH:16]2[C:40]([O:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:41])=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10387Benzyl chloroformateHCID 19960897N-cyclohexyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboxamide methanesulfonate

Product 1

HCID 19960831HCID 19960831, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

30 g of N-cyclohexyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboxamide methanesulfonate was added to a solution of 300 ml of chloroform and 16.23 g of triethylamine and the resulting mixture was stirred at room temperature for 1 hour. Then 41.5 ml of benzyloxycarbonyl chloride was added thereto under ice-cooling and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with 20 ml of water thrice and dried over magnesium sulfate. The reaction mixture was distilled under reduced pressure and the residue was separated by silica gel column chromatography (solvent: chloroform). Thus 23.6 g of N-cyclohexyl-2-(benzyloxycarbonyl)-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboxamide (yield: 87%) was obtained. The NMR data of this product were as follows. It was confirmed that this product is N-cyclohexyl-2-(benzyloxycarbonyl)-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboxamide.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe resulting mixture was stirred at room temperature for 3 hours
  3. washThe reaction mixture was washed with 20 ml of water thrice
  4. dry with materialdried over magnesium sulfate
  5. distillationThe reaction mixture was distilled under reduced pressure
  6. customthe residue was separated by silica gel column chromatography (solvent: chloroform)

Sources & evidence

ORD record
ord-21bf75c1f1594bcd81dde471b3f59869
Source dataset
uspto-grants-1997_04
Patent number
US05621103

Reaction notes

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