Pyridine → tert-Butyl (1-acetylpiperidin-4-yl)carbamate

HRID 49769Notes

Reaction equation

HRID 49769 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>ClCCl>[C:21]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 22741830tert-Butyl (1-acetylpiperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of O-tert-butyl N-(piperidin-4-yl)carbamate (4.0 g) in dichloromethane (40 ml) were added pyridine (1.94 ml), dichloromethane (40 ml), acetic anhydride (20.8 ml) and then N,N-dimethylaminopyridine (0.1 g) at ambient temperature. After stirring for 3 hours, the mixture was washed with 0.1N hydrochloric acid, water, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. After rinse with diisopropyl ether, O-tert-butyl N-(1-acetylpiperidin-4-yl)carbamate (4.01 g) was obtained.

Workup

  1. customat ambient temperature
  2. washthe mixture was washed with 0.1N hydrochloric acid, water, and brine
  3. dry with materialAfter drying with magnesium sulfate
  4. customthe solvents were removed under reduced pressure
  5. washAfter rinse with diisopropyl ether

Sources & evidence

ORD record
ord-b12d37f21ea84368a39ce8b587735be1
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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