Acetic Anhydride → HCID 11100967, compound

HRID 977163Notes

Reaction equation

HRID 977163 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]([CH3:31])([CH3:30])[CH2:27][NH:28][CH3:29])[CH2:22][CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Na+].CC1C=CC(S([O-])(=O)=O)=CC=1>ClCCl.C(N(CC)CC)C>[CH3:29][N:28]([CH2:27][C:26]([CH3:31])([CH:23]1[CH2:24][CH2:25][N:20]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:21][CH2:22]1)[CH3:30])[C:5](=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 85570p-ToluenesulfonateHCID 11759565HCID 11759565, compound

Product 1

HCID 11100967HCID 11100967, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3.4 ml (3.6×10-2 mole) of acetic anhydride was added to a solution of 8 g (2.4×10-2 mole) of 1-dodecyl-N,β,β-trimethyl-4-piperidineethanamine in 100 ml of dichloromethane and 16.8 ml of N,N-diethylethanamine. The reaction mixture was stirred for 12 hours at room temperature. The solution was poured into a 1N sodium hydroxide solution and extracted with trichloromethane. The organic phase was washed with water, dried and filtered and the solvents were evaporated off under reduced pressure. 8.7 g of N-methyl-N-[2-methyl-2-[(1-dodecyl)-4-piperidinyl]propyl]acetamide (yield: 97%) was obtained, from which the 4-methylbenzene sulphonate was prepared and recrystallised from ethyl acetate. M Pt=102°-103° C.

Workup

  1. extractionextracted with trichloromethane
  2. washThe organic phase was washed with water
  3. customdried
  4. filtrationfiltered
  5. customthe solvents were evaporated off under reduced pressure

Sources & evidence

ORD record
ord-e04cc752d671495b92858cd4a5fff989
Source dataset
uspto-grants-1997_03
Patent number
US05614534

Reaction notes

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