Ammonia → 5-(Chloromethyl)-2-phenyl-1,3-oxazolidine

Reaction equation

[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([CH:11]1O[CH2:12]1)[Cl:10].[NH3:14]>>[C:2]1([CH:1]2[NH:14][CH2:12][CH:11]([CH2:9][Cl:10])[O:8]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 240Benzaldehyde

HCID 7835Epichlorohydrin

Product 1

HCID 2707015-(Chloromethyl)-2-phenyl-1,3-oxazolidineYield 20%

Procedure

According to Carter and Blattacharye [J. Amer. Chem. Soc 75, 2503 (1953)], D,L-carnitine is obtained by reacting benzaldehyde, epichlorohydrin and ammonia in an organic solvent, the reaction product 2-phenyl-5-chloromethyloxazolidine is isolated and said compound is subsequently transformed into D,L-carnitine according to known techniques, with a yield of 20-25%.

Sources & evidence

ORD record: ord-7005e47fe6954e10b169843c7524f5f6
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04664852

Reaction notes

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