Acetaldehyde → HCID 19418793, compound

HRID 864385Notes

Reaction equation

HRID 864385 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])[CH2:13][CH2:12]1)=[O:10])[CH3:7].[CH:25](=O)[CH3:26]>CO>[CH3:7][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][CH2:25][CH3:26])[CH2:13][CH2:12]1)=[O:10])[CH3:5]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19418793HCID 19418793, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (1.6 g) is added to a 0° solution of 1-[1,1-dimethylethoxycarbonyl]-4-(2-aminophenyl)piperazine (PREPARATION 13, 6.52 g) and acetaldehyde (1.48 ml) dissolved in methanol (65 ml). After 3 hr the reaction mixture is partially concentrated under reduced pressure. Then it is diluted with chloroform, washed with saturated aqueous sodium bicarbonate, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, Rf =0.62 (ethyl acetate/hexane, 1/1), NMR (300 MHz, CDCl3) 7.04, 6.95, 6.66, 4.59, 3.70-3.50, 3.15, 2.82, 1.49 and 1.28δ.

Workup

  1. concentrationAfter 3 hr the reaction mixture is partially concentrated under reduced pressure
  2. additionThen it is diluted with chloroform
  3. washwashed with saturated aqueous sodium bicarbonate, saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7719c1a027f44af8982725764d0bfbe9
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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