Acetic Acid → HCID 21849454, compound

HRID 862841Notes

Reaction equation

HRID 862841 reaction equation
N[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].C=O.[C:33]([BH3-])#[N:34].[Na+].[C:37](O)(=O)C>C(#N)C>[C:5]([O:4][CH2:3][C:2]([N:34]([CH3:33])[CH3:37])([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])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21849148HCID 21849148, compound

Product 1

HCID 21849454HCID 21849454, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-1,3-diacetoxy-2-octadecylpropane (700 mg) was dissolved in 35 ml of acetonitrile and 1.38 g of 37% formaldehyde and 330 mg of sodium cyanoborohydride were added thereto. The mixture was stirred at room temperature for 1 hour. Acetic acid (0.265 ml) was added thereto and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and purified by silica gel column chromatography using hexane-ethyl acetate (4:1→3:1) as an eluent to give 436 mg of colorless, oily 1,3-diacetoxy-2-(N,N-dimethylamino)-2-octadecylpropane.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed24ff531b184e1eb4165a5c5cf8f5f3
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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