Ethanol → HCID 67444892, compound

HRID 1666827Notes

Reaction equation

HRID 1666827 reaction equation
C([Cl:4])(=O)C.C(O)C.[F:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[CH:23]=1>C(OCC)C>[ClH:4].[F:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]([F:33])([F:31])[F:32])[CH:23]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 21071661HCID 21071661, compound

Product 1

HCID 67444892HCID 67444892, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add dropwise acetyl chloride (2.3 ml, 32.4 mmol) to anhydrous ethanol (50 mL) and stir the solution for 10 min at ambient temperature and add to a solution N-(2-(7-fluoro-1H-indol-3-yl)ethyl)-3-(2,2,2-trifluoroethoxy)benzylamine (10.7 g, 29.2 mmol) in diethyl ether. Concentrate the resulting solution under reduced pressure to give a yellow solid. Recrystallize the yellow solid from ethyl acetate/methanol to give the title compound: mp 163-164° C.; MS (m/e): 367 (M−1), 365 (M−1); Calculated for C19H18F4N2O HCl: Calcd: C, 56.65; H, 4.75; N, 6.95. Found: C, 56.45; H, 4.54; N, 6.90.

Workup

  1. concentrationConcentrate the resulting solution under reduced pressure
  2. customto give a yellow solid
  3. customRecrystallize the yellow solid from ethyl acetate/methanol

Sources & evidence

ORD record
ord-1b82ad8900124570b7eb490963eb945c
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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