Acetyl chloride → HCID 66938718, compound

HRID 1716882Notes

Reaction equation

HRID 1716882 reaction equation
C([Cl:4])(=O)C.C(OC(=O)[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]([CH3:26])[CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH:13]=1)(C)(C)C>CO>[ClH:4].[ClH:4].[ClH:4].[CH3:25][N:22]1[CH2:21][CH2:20][CH:19]([N:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH2:11])[CH:13]=2)[CH3:26])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58997344HCID 58997344, compound

Product 1

HCID 66938718HCID 66938718, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine acetyl chloride (5 mL) with dried methanol (10 mL) at 0° C. under nitrogen atmosphere. Stir for 1 hr. at 0° C. Add a solution of (3-(methyl-(1-methylpiperidin-4-yl)amino)phenyl)carbamic acid tert-butyl ester (Preparation 10, 990 mg, 3.1 mmol) in methanol (2 mL). Stir overnight. Concentrate under reduced pressure. Triture with diethyl ether (1 mL) to provide the title intermediate (671 mg, 66%): mass spectrum (free base, ion spray): m/z=220.3 (M+1). Analysis calculated for C13H24Cl3N3Cl3: C, 47.50; H, 7.36; N, 12.78. Found: C, 47.28; H, 7.28; N, 12.46.

Workup

  1. customat 0° C.
  2. customat 0° C
  3. stirringStir overnight
  4. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-7cb7c837a544412eb20c12fd1a200ca6
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

Loading…