Acetyl chloride → tert-Butyl 4-[acetyl(methyl)amino]piperidine-1-carboxylate

HRID 506857Notes

Reaction equation

HRID 506857 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](Cl)(=[O:18])[CH3:17]>ClCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([C:16](=[O:18])[CH3:17])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Product 1

HCID 22061331tert-Butyl 4-[acetyl(methyl)amino]piperidine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

To a solution of 4-methylamino-piperidine-1-carboxylic acid tert-butyl ester (616 mg, 2.9 mmol) in CH2 Cl2 (25 ml), was added acetyl chloride (215 μl, 3.02 mmol, 1.05 eq.) dropwise. The reaction mixture was stirred at RT for 16 hrs. The crude reaction mixture was extracted with CH2 Cl2 (2×50 ml) and washed with water (10 ml) and with brine (10 ml). The solvent was removed under reduced pressure to give the expected 4-(Acetyl-methyl-amino)-piperidine-1-carboxylic acid tert-butyl ester (708 mg, 96% yield).

Workup

  1. customThe crude reaction mixture
  2. extractionwas extracted with CH2 Cl2 (2×50 ml)
  3. washwashed with water (10 ml) and with brine (10 ml)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eea0e9ef877b4ac0ae851af889d5d769
Source dataset
uspto-grants-2010_08
Patent number
US07786121B2

Reaction notes

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