Acetaldehyde → HCID 58786604, compound

HRID 1376038Notes

Reaction equation

HRID 1376038 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27](=O)[CH3:28].C([BH3-])#N.[Na+].[CH3:34][CH2:35]O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:25])([F:26])[F:24])[CH2:15][N:16]([CH2:27][CH3:28])[CH2:34][CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 177Acetaldehyde2×HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 587865401,1-Dimethylethyl 4-[2-amino-1-[2-(trifluoromethyl)phenyl]ethyl]-1-piperazinecarboxylate

Product 1

HCID 58786604HCID 58786604, compoundYield 99%

Procedure

To a solution of a 4-[2-Amino-1-(2-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (204) (0.75 g, 2.01 mmol) in EtOH (50 mL) was added acetaldehyde (3.37 mL, 60.3 mmol) via RT distillation (warming flask with hand). Halfway through the addition of the acetaldehyde, sodium cyanoborohydride (0.631 g, 10.05 mmol) was added. The reaction was allowed to stir at room temperature for 18 h. The reaction mixture was concentrated to dryness. The resulting residue was taken up in EtOAc (50 mL) and washed with sat. NaHCO3 (50 ml) and brine (50 mL). The organic phase was concentrated to dryness yielding 0.860 g (99%) product.

Workup

  1. distillationdistillation (warming flask with hand)
  2. additionwas added
  3. concentrationThe reaction mixture was concentrated to dryness
  4. washwashed with sat. NaHCO3 (50 ml) and brine (50 mL)
  5. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-f210858960cf41bc9041042c22462c83
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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