Aniline → 1-Phenyl-pyrrolidin-3-ol

HRID 2248841Notes

Reaction equation

HRID 2248841 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][CH:10]([OH:14])[CH2:11][CH2:12]Br>>[C:2]1([N:1]2[CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 295701,4-Dibromo-2-butanol

Product 1

HCID 111711521-Phenyl-pyrrolidin-3-ol

Procedure

Referring to the above reaction diagram, tetrahydroquinoline may be alkylated in methanol by adding excess bromoethanol, sodium iodide and potassium carbonate and refluxing the solution for 24 hours. The product is preferably isolated in water and purified by vacuum distillation. If phenylpiperazine is the starting material, it is alkylated under the same reaction conditions. A 1-phenyl-4-piperidinol structure is synthesized by preparing N-but-3-enyl--N-methylaniline, and treating with aqueous trifluoroacetic acid. N-but-3-enyl--N-methylaniline is provided by alkylation of N-methylaniline with 4-bromobut-1-ene. 1-Phenyl-3-pyrrolidinol is synthesized by the reaction of aniline with 1,4-dibromo-2-butanol.

Sources & evidence

ORD record
ord-3491e42710964fba94c1ac62ce342fa1
Source dataset
uspto-grants-1991_08
Patent number
US05041509

Reaction notes

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