Ethanol → HCID 21071663, compound

HRID 1371885Notes

Reaction equation

HRID 1371885 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:35])([F:34])[CH:31]([F:33])[F:32])[CH:23]=1>C(OCC)(=O)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:35])([F:34])[CH:31]([F:33])[F:32])[CH:23]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 21071662HCID 21071662, compound

Product 1

HCID 21071663HCID 21071663, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add acetyl chloride (2.4 mL, 33.8 mmol) dropwise to anhydrous ethanol (50 mL) and stir the solution for 10 min at ambient temperature and add to a solution of N-(2-(7-fluoro-1H-indol-3-yl)ethyl)-3-(2,2,3,3-tetrafluoropropoxy)benzylamine (12.0 g, 30.1 mmol) in ethyl acetate. Concentrate the resulting solution under reduced pressure to give a yellow solid. Recrystallize the yellow solid from ethyl acetate/ethanol/diethyl ether to give the title compound: mp 142–143° C. MS(m/e): 399 (M+1), 397 (M−1). Calculated for C20H19F5N2O.HCl: Calcd: C, 55.24; H, 4.64; N, 6.44. Found: C, 55.44; H, 4.66; N, 6.46.

Workup

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

Sources & evidence

ORD record
ord-152277356ce94e50bc2330d0c6c83b4d
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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