Acetyl chloride → HCID 66938718, compound

HRID 1591859Notes

Reaction equation

HRID 1591859 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-b10edfb5699a4632b10210739eb7e3df
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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