{4-[4-(2-Dimethylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester → 4-[4-(2-Dimethylaminoethoxy)phenyl]butylamine

HRID 1161973Notes

Reaction equation

HRID 1161973 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:17][CH:16]=1)C1C=CC=CC=1>[Pd].CO>[CH3:26][N:24]([CH3:25])[CH2:23][CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 66849448{4-[4-(2-Dimethylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

Product 1

HCID 221799624-[4-(2-Dimethylaminoethoxy)phenyl]butylamineYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The protected amine 62 (0.552 g, 1.5 mmol) was stirred with 10% palladium on carbon (0.127 g, wet) in methanol (50 mL) at room temperature for 3.5 h under hydrogen (1 atm). After this time, the catalyst was filtered off and the solvent was removed under reduced pressure to give the free amine 63 (0.27 g, 77%) as a white powder. 1H NMR (300 MHz, CD3OD) δ 1.55 (m, 4H), 2.32 (s, 6H), 2.54 (m, 2H), 2.75 (m, 2H), 4.02 (m, 2H), 6.78 (d, 2H), 7.08 (d, 2H).

Workup

  1. filtrationAfter this time, the catalyst was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6b22a850e6044d6dacc98304cbe14cd3
Source dataset
uspto-grants-2010_10
Patent number
US07820678B2

Reaction notes

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