N,N-Dimethylaniline → HCID 21849166, compound

HRID 1451601Notes

Reaction equation

HRID 1451601 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. IRν max (CHCl3): 3450, 3400, 2920, 2850, 1740, 1680, 1520, 1460, 1380, 1240, 1020 cm-1 1 H-NMR (CDCl3 /TMS) δ: 0.879 (3H, t, J=6.8 Hz), 0.918 (3H, t, J=7.4 Hz), 1.251 (34H, m), 1.6 (4H, m), 2.078 (6H, s), 2.150 (2H, t, J=7.2 Hz), 4.271 (2H, d, J=11.6 Hz), 4.330 (2H, d, J=11.6 Hz), 5.599 (1H, s)

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-ed12208b1aa6454cb01efd36fc2d6b8f
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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