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

HRID 2353969Notes

Reaction equation

HRID 2353969 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]([C:31](=[O:33])[CH3:32])[CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:10]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:9]1=2)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=1)[CH2:16][N:15]([CH:11]1[CH2:12][CH2:13][CH2:14][NH:8][C:9]2[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:10]1=2)[C:31](=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 590031075-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59003177N-(3,5-Bis-trifluoromethyl-benzyl)-N-(8-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (7.9 g, 14.0 mmol) in dichloromethane (100 mL) add a solution of trifluoroacetic acid (50 mL) in dichloromethane (50 mL). After stirring at room temperature for 1 h, neutralize the reaction with concentrated sodium bicarbonate. Separate the organic phase and wash with water (100 mL) and brine (100 μL). Dry the organics over sodium sulfate, filter, and remove solvent under vacuum. Crystallize the compound from dichloromethane/hexane. This provides the title compound (5.3 g, 81%) as a colorless solid: MS (ES+): 465 (M+H).

Workup

  1. customSeparate the organic phase
  2. washwash with water (100 mL) and brine (100 μL)
  3. dry with materialDry the organics over sodium sulfate
  4. filtrationfilter
  5. customremove solvent under vacuum
  6. customCrystallize the compound from dichloromethane/hexane

Sources & evidence

ORD record
ord-3b3d6b2576354598815cf742aee3f563
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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