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Pyridine → N-(1-Acetyl-8-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-acetamide

HRID 2353971
Notes
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Reaction equation

HRID 2353971 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].CN(C1C=CC=CN=1)C.N1C=CC=CC=1.[F:20][C:21]([F:50])([F:49])[C:22]1[CH:23]=[C:24]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:25][N:26]([CH:30]1[CH2:36][CH2:35][CH2:34][NH:33][C:32]2[CH:37]=[C:38]([Cl:41])[CH:39]=[CH:40][C:31]1=2)[C:27](=[O:29])[CH3:28]>ClCCl>[C:1]([N:33]1[CH2:34][CH2:35][CH2:36][CH:30]([N:26]([CH2:25][C:24]2[CH:42]=[C:43]([C:45]([F:46])([F:47])[F:48])[CH:44]=[C:22]([C:21]([F:20])([F:49])[F:50])[CH:23]=2)[C:27](=[O:29])[CH3:28])[C:31]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:32]1=2)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 218852-DimethylaminopyridineHCID 59003177N-(3,5-Bis-trifluoromethyl-benzyl)-N-(8-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Product 1

HCID 59003196N-(1-Acetyl-8-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-acetamide
Yield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add acetyl chloride (0.3 mmol) followed by dimethylaminopyridine (cat.) and pyridine (0.3 mmol) to a solution of N-(3,5-Bis-trifluoromethyl-benzyl)-N-(8-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.05 g, 0.11 mmol) in dichloromethane (1 ml). After stirring for 14-16 h dilute with dichloromethane (2 mL) and wash with 5% HCl (2 mL), water (2 mL) and brine (2 mL). Dry the organics over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the crude product over silica gel using ethyl acetate/hexane (10-30%) to elute. This afford the title compound (0.04 g, 89%) as a colorless solid: MS (ES+): 507 (M+H).

Workup

  1. washwash with 5% HCl (2 mL), water (2 mL) and brine (2 mL)
  2. dry with materialDry the organics over sodium sulfate
  3. filtrationfilter
  4. customremove solvent under vacuum
  5. washto elute

Sources & evidence

ORD record
ord-05527076ac39450292df252249039a8a
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07749992B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes