Hydrochloric Acid → 4-(Isoquinolin-1-yl)-1-methylpiperidin-4-ol

HRID 1112356Notes

Reaction equation

HRID 1112356 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([O:19]C(=O)C2C=CC=CC=2)([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][CH2:4]1.[H-].[Na+].CN1CCC(=O)CC1.Cl>CN(C)C=O>[CH3:2][N:3]1[CH2:4][CH2:5][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)([OH:19])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 740491-Methyl-4-piperidoneHCID 22763839HCID 22763839, compound

Product 1

HCID 3194124-(Isoquinolin-1-yl)-1-methylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

346 g. of 1-methyl-4-benzoyloxy-4-(1-isoquinolyl)-piperidine hydrochloride (m.p. 269°, from isopropanol), obtainable by adding 30 g. of NaH in portions to a solution of 260 g. of 1-cyano-2-benzoyl-1,2-dihydroiosquinoline and 120 g. of 1-methylpiperidin-4-one in 950 ml. of dimethylformamide, with stirring, and allowing the mixture to stand overnight, are heated under reflux with 1,400 ml. of 25% hydrochloric acid for 40 hours. The mixture is cooled and worked up in the customary manner to give 1-methyl-4-(1-isoquinolyl)-piperidin-4-ol, m.p. 265°-266°.

Workup

  1. temperatureare heated
  2. temperatureunder reflux with 1,400 ml
  3. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-3820646285024ec899e15d5a79f93d78
Source dataset
uspto-grants-1978_10
Patent number
US04122180

Reaction notes

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