Hydrochloric Acid → 2-(Dimethylaminophenylmethyl)cyclohexanol

HRID 1596032Notes

Reaction equation

HRID 1596032 reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:13])[CH3:5].Cl>CO>[CH3:5][N:4]([CH:6]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[OH:13])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 112647962-(Dimethylaminophenylmethyl)cyclohexanolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A total of 28.3 g (747 mmole) sodium borohydride, dissolved in 650 ml methanol, were added in portions to 80.0 g (299 mmole) of the 2-(dimethylaminophenylmethyl)-cyclohexanone prepared according to Example 1 (2nd stage), and the mixture was subsequently stirred for one hour. For working up, 680 ml dilute hydrochloric acid (1 N) were added, and the mixture was extracted with 500 ml ether. The aqueous phase was rendered alkaline (pH≧10) with 25 vol. % ammonia solution and extracted three times with 250 ml ether each time. The combined organic extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar). 65.2 g (94% of theoretical) 2-(dimethylaminophenylmethyl)cyclohexanol were obtained.

Workup

  1. customprepared
  2. extractionthe mixture was extracted with 500 ml ether
  3. extractionextracted three times with 250 ml ether each time
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator (500 to 10 mbar)

Sources & evidence

ORD record
ord-c0b070277cf041b4a180332599ad1408
Source dataset
uspto-grants-2001_09
Patent number
US06288278B1

Reaction notes

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