1-Benzyl-4-piperidone → (1-Benzyl-4-isoquinolin-1-ylpiperidin-4-yl) benzoate

HRID 1112358Notes

Reaction equation

HRID 1112358 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C2C(=CC=CC=2)C=CN1[C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)#N.C(N1CCC(=O)CC1)C1C=CC=CC=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:14][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 2304882-Benzoyl-1,2-dihydro-1-isoquinolinecarbonitrileHCID 134662361-Benzyl-4-(1-isoquinolyl)-piperidin-4-ol

Product 1

HCID 319768(1-Benzyl-4-isoquinolin-1-ylpiperidin-4-yl) benzoate

Procedure

A solution of 318 g. of 1-benzyl-4-(1-isoquinolyl)-piperidin-4-ol, obtainable by reacting 1-cyano-2-benzoyl-1,2-dihydroisoquinoline with 1-benzylpiperidin-4-one to give 1-benzyl-4-benzoyloxy-4-(1-isoquinolyl)-piperidine, which is subsequently hydrolyzed in 5 l. of methanol, is hydrogenated on 60 g. of 5% Pd-on-charcoal at 20° under 1 atmosphere of hydrogen. The mixture is filtered and the filtrate is evaporated to give 4-(1-isoquinolyl)-piperidin-4-ol, m.p. 138°-140°.

Sources & evidence

ORD record
ord-04a220ec7b594887b658916e52588940
Source dataset
uspto-grants-1978_10
Patent number
US04122180

Reaction notes

Loading…