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

HRID 1085183Notes

Reaction equation

HRID 1085183 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-e8ba622cc6544cfcaa819493d9704703
Source dataset
uspto-grants-1991_04
Patent number
US05008257

Reaction notes

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