Gamma-Aminobutyric Acid → Benzyl 4-aminobutanoate--hydrogen chloride (1/1)

HRID 2082001Notes

Reaction equation

HRID 2082001 reaction equation
[CH2:1]([CH2:6][NH2:7])[CH2:2][C:3]([OH:5])=[O:4].[CH2:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O=S(Cl)[Cl:18]>C(OCC)C>[ClH:18].[CH2:8]([O:4][C:3](=[O:5])[CH2:2][CH2:1][CH2:6][NH2:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 244Benzyl AlcoholHCID 24386Thionyl Chloride

Product 1

HCID 18707498Benzyl 4-aminobutanoate--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

GABA (4 g, 38.8 mmol) was suspended in 50 ml (0.48 mol) of benzyl alcohol. The reaction mixture was stirred, with cooling on an ice bath, while 20 ml SOCl2 was added dropwise over a 30 minute period. The mixture was slowly brought to the reflux temperature and refluxed for 4 hours. The resultant pink viscous solution was cooled to room temperature. Addition of 50 ml of ethyl ether and refrigeration overnight produced white crystals which were collected by filtration, recrystallized from a mixture of ethyl ether and ethanol and dried, m.p. 115°-116° C.

Workup

  1. additionwas added dropwise over a 30 minute period
  2. temperaturerefluxed for 4 hours
  3. customproduced white crystals which
  4. filtrationwere collected by filtration
  5. customrecrystallized from a mixture of ethyl ether and ethanol
  6. customdried

Sources & evidence

ORD record
ord-624349f1cfc04b75bd2e2821a75921e6
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

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