Benzaldehyde → 4-Benzylamino-1-Butanol

HRID 1952977Notes

Reaction equation

HRID 1952977 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H][H]>O=[Pt]=O.C(O)C>[C:8]1([CH2:7][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 258684-Amino-1-butanolHCID 178418361HCID 178418361, compound

Product 1

HCID 17900184-Benzylamino-1-ButanolYield 98.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Dissolve diaminooctane (10.8 g, 0.075) in methylene chloride (200 mL), methanol (100 mL) with di-t-butyldicarbonate (32.7 g, 0.156 mol). Stir the reaction overnight. Concentrate the reaction under vacuum and crystallize the residue from hexane to provide N, N'-bis(t-butoxycarbonyl)-1,8-octanediamine (20.2 g), mp 96-97° C. Combine 4-amino-butan-1-ol (8.9 g, 0.1 mol), benzaldehyde (10.6 g, 0.1 mol), ethanol (100 mL) and PtO2 (0.3 g) and hydrogenate at 45 lbs./sq. in. until hydrogen is no longer taken up. Filter the reaction and concentrate the filtrate under vacuum to provide 4-[[(phenyl)methyl]amino]-butan-1-ol (17.7 g), Rf =0.70 eluting with 10% conc. NH3 /methanol.

Workup

  1. filtrationFilter
  2. customthe reaction
  3. concentrationconcentrate the filtrate under vacuum

Sources & evidence

ORD record
ord-994281198ae34abeaf9ade1f582dd12c
Source dataset
uspto-grants-2000_09
Patent number
US06114394

Reaction notes

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