Benzyl Chloride → 2,2'-((Phenylmethyl)imino)bisethanol
Reaction equation
Cl.C(N1CCC(C2C=CC=CC=2)(C#N)CC1)C1C=CC=CC=1.CCOC([C:28]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)CCNCC1)=O.C(Cl)C1C=CC=CC=1.[OH:48][CH2:49][CH2:50][NH:51][CH2:52][CH2:53][OH:54]>>[OH:48][CH2:49][CH2:50][N:51]([CH2:28][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:52][CH2:53][OH:54]Participants
5
Procedure
Eisleb in Example 2 of U.S. Patent 2,167,351, issued July 25, 1939, shows the preparation of 1-benzyl-4-phenylpiperidine-4-carbonitrile hydrochloride, m.p. 259°-260° C., as an intermediate for normeperidine, namely, ethyl 4-phenylpiperidine-4-carboxylate, by first reacting benzyl chloride with N,N-bis(2-hydroxyethyl)amine to produce N,N-bis(2-hydroxyethyl)benzylamine, next reacting the latter compound with thionyl chloride to produce N,N-bis(2-chloroethyl)benzylamine and isolating it in free base form as "an oil of feebly brownish color"; and then heating N,N-bis(2-chloroethyl)benzylamine with benzyl cyanide (same as phenylacetonitrile) in toluene in the presence of sodium amide (same as sodamide).
Sources & evidence
- ORD record
- ord-0c90d34a57ee46849d0002fa35ed7c6b
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04748276
Reaction notes
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