p-Toluenesulfonic acid → 4-(1-Benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenethyl alcohol

HRID 1005008Notes

Reaction equation

HRID 1005008 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 149034381-Benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol

Product 1

HCID 221264074-(1-Benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenethyl alcohol

Procedure

In an analogous manner to that described in Example 22(b), by an elimination reaction from 1-benzyl-4-[4-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol using p-toluenesulphonic acid there was obtained 2-[4-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-ethanol as a colourless oil; MS: 293 (M)+.

Sources & evidence

ORD record
ord-17c1367bdd98454499cda59b1c94d67d
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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