Acetic Anhydride → HCID 22763844, compound

HRID 1112359Notes

Reaction equation

HRID 1112359 reaction equation
[C:1]1([C:11]2([OH:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[C:18](OC(=O)C)(=O)[CH3:19].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C(Cl)(Cl)Cl.C1COCC1.C1C=CC=CC=1.N1C=CC=CC=1>[CH2:18]([N:14]1[CH2:13][CH2:12][C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][N:2]=2)([OH:17])[CH2:16][CH2:15]1)[CH3:19]

Participants

9

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22763836HCID 22763836, compound

Product 1

HCID 22763844HCID 22763844, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.28 g. of 4-(1-isoquinolyl)-piperidin-4-ol, 1 ml. of pyridine, 1 ml. of acetic anhydride and 20 ml. of benzene is stirred for 3 hours at 25°. The crude 1-acetyl-4-(1-isoquinolyl)-piperidin-4-ol obtained after the customary work up is heated under reflux with 0.7 g. of LiAlH4 in 40 ml. of THF for 24 hours, under nitrogen. The mixture is worked up with sodium hydroxide solution and chloroform in the customary manner to give 1-ethyl-4-(1-isoquinolyl)-piperidin-4-ol, m.p. 275°-276°.

Workup

  1. additionA mixture of 2.28 g
  2. customThe crude 1-acetyl-4-(1-isoquinolyl)-piperidin-4-ol obtained after the customary work
  3. temperatureup is heated
  4. temperatureunder reflux with 0.7 g

Sources & evidence

ORD record
ord-2b0b0bfd7d9d40029e77c6635392535a
Source dataset
uspto-grants-1978_10
Patent number
US04122180

Reaction notes

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