Oxalyl chloride → HCID 10167445, compound

HRID 1270198Notes

Reaction equation

HRID 1270198 reaction equation
[CH:1]1([C:7]2[CH:28]=[CH:27][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[CH:24]=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:29](Cl)(=[O:33])[C:30](Cl)=[O:31].[CH2:35]1[CH2:40][CH2:39][N:38]([CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH2:37][CH2:36]1>ClCCl>[N:38]1([CH:41]2[CH2:46][CH2:45][N:44]([C:29](=[O:33])[C:30]([C:24]3[N:16]4[C:15]([CH2:14][N:13]([C:11](=[O:12])[C:10]5[CH:27]=[CH:28][C:7]([CH:1]6[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]6)=[CH:8][CH:9]=5)[C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[CH2:17]4)=[CH:26][CH:25]=3)=[O:31])[CH2:43][CH2:42]2)[CH2:39][CH2:40][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 786071,4'-BipiperidineHCID 10177192HCID 10177192, compound

Product 1

HCID 10167445HCID 10167445, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Example 4 (1.0 g) in dichloromethane (20 mL) was added oxalyl chloride (0.34 g). The reaction mixture was allowed to stir at room temperature for three hours, and then 4-(1-piperidino) piperidine (0.91 g) was added. After stirring overnight at room temperature, the mixture was washed with water and saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol® and the eluate refluxed with the slow addition of hexane to provide the title compound as pale pink crystals (0.43 g), m.p. 190–195° C.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. washthe mixture was washed with water and saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solution was filtered through a short column of Magnesol®
  5. temperaturethe eluate refluxed with the slow addition of hexane

Sources & evidence

ORD record
ord-7a9128b6d3464c4c8c0f06c2082d741b
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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