N,N-Dimethylaniline → HCID 21849166, compound

HRID 862838Notes

Reaction equation

HRID 862838 reaction equation
[NH2:1][C:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH2:8][O:9][C:10](=[O:12])[CH3:11])[CH2:3][O:4][C:5](=[O:7])[CH3:6].CN(C)C1C=CC=CC=1.[C:40](Cl)(=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44]>CCOCC.C(OCC)(=O)C>[C:5]([O:4][CH2:3][C:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([NH:1][C:40](=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44])[CH2:8][O:9][C:10](=[O:12])[CH3:11])(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 61186Valeryl chlorideHCID 21849148HCID 21849148, compound

Product 1

HCID 21849166HCID 21849166, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-1,3-diacetoxy-2-octadecylpropane (1.0 g) was dissolved in 50 ml of dry ether and 425 mg of N,N-dimethylaniline and 500 mg of pentanoyl chloride were added thereto. The mixture was stirred at room temperature under a nitrogen atmosphere for 6 hours. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried and the resultant mixture was concentrated. The concentrate was purified by silica gel column chromatography using hexane-ethyl acetate (5:1→2:1) as an eluent to give 1.036 g of colorless, oily 1,3-diacetoxy-2-octadecyl-2-(N-pentanoylamino)propane.

Workup

  1. washwashed with 1N hydrochloric acid
  2. customThe organic layer was dried
  3. concentrationthe resultant mixture was concentrated
  4. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dbc557f4e9ee49d7b6be4ebbe99a282b
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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