Ethyl 3-(benzylamino)-3-methylbutanoate hydrochloride → Ethyl 3-amino-3-methylbutanoate hydrochloride

HRID 1263063Notes

Reaction equation

HRID 1263063 reaction equation
[ClH:1].C([NH:9][C:10]([CH3:18])([CH3:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])C1C=CC=CC=1>[Pd]>[ClH:1].[NH2:9][C:10]([CH3:18])([CH3:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 1

HCID 20255210Ethyl 3-(benzylamino)-3-methylbutanoate hydrochloride

Product 1

HCID 15578558Ethyl 3-amino-3-methylbutanoate hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 25 g (0.1 mole) of ethyl 3-(N-benzylamino)-3-methylbutyrate hydrochloride and approximately 2 g of 10% Pd-C in 250 ml of dried USP alcohol was hydrogenated under 55 psi H2 for four days. The reaction medium was then filtered and evaporated under reduced pressure to provide 18 g (100%) of an amber oil which gradually crystallized upon standing: mp 82°-83° C.; NMR (CD3OD) δ1.2 (t, J=7, Hz, 3, --CH2CH3) 1.5 (s, 6, two --CH3), 2.8 (s, 2, --CH2 --), 4.2 (q, J=7 Hz, 2, --CH2CH3). Analysis Calculated for C7H16NO2Cl: C, 46.28; H, 8.88; N, 7.71. Found: C, 46.46; H, 8.98; N, 7.90.

Workup

  1. filtrationThe reaction medium was then filtered
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d29001d3cba040d2a6843ea260a20cb9
Source dataset
uspto-grants-1984_06
Patent number
US04455317

Reaction notes

Loading…