Hydrochloric Acid → 4-Phenyl-alpha,alpha,1-trimethyl-4-piperidinemethanol

HRID 1980094Notes

Reaction equation

HRID 1980094 reaction equation
[C:1]1([C:7]23[CH2:16][CH:11]([O:12][C:13]2([CH3:15])[CH3:14])[N:10]([CH3:17])[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].[BH4-].Cl.[OH-].[Na+]>CO.C(O)(=O)C>[C:1]1([C:7]2([C:13]([CH3:15])([CH3:14])[OH:12])[CH2:8][CH2:9][N:10]([CH3:17])[CH2:11][CH2:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28123BorohydrideHCID 5003444Sodium cyanoborohydrideHCID 540271932,6,6-Trimethyl-5-phenyl-7-oxa-2-azabicyclo[3.2.1]octane

Product 1

HCID 133634034-Phenyl-alpha,alpha,1-trimethyl-4-piperidinemethanolYield 66.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1.47 g of the above product III in a mixture of 10 mL of methanol and 2 mL of acetic acid was cooled with ice and treated with 0.76 g of sodium cyanoborohydride. The mixture was stirred at room temperature for 2 h, and the excess borohydride was decomposed by addition, with ice cooling, of 8 mL of conc hydrochloric acid. After stirring at room temperature for 0.5 h the mixture was made basic with aqueous sodium hydroxide solution and extracted with methylene chloride. Removal of the solvent from the dried solution and crystallization of the residue from ethyl acetate gave 0.98 g of 4-phenyl-α,α,1-trimethyl-4-piperidinemethanol, m.p. 146°-147°. NMR (220 MHz in CDCl3): τ 2.7-2.8 (m, 5H); 7.0-8.2 (m, 9H); 8.0 (s, 3H) and 8.9 (s, 6H). Anal. Calcd. for C15H23NO: C, 77.21; N, 9.94; N, 6.00. Found: C, 77.12; H, 9.89; N, 6.00.

Workup

  1. temperaturewas cooled with ice
  2. stirringAfter stirring at room temperature for 0.5 h the mixture
  3. extractionextracted with methylene chloride
  4. customRemoval of the solvent
  5. customfrom the dried solution and crystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-fd47c0fcaa9c48a084c2ae5f515acf12
Source dataset
uspto-grants-1984_11
Patent number
US04485109

Reaction notes

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