Hydrochloric Acid → HCID 178479224, compound

HRID 377093Notes

Reaction equation

HRID 377093 reaction equation
B.[NH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10](O)=[O:11])[CH2:6][CH2:5]1.[ClH:13]>O1CCCC1>[ClH:13].[NH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 178511262HCID 178511262, compound

Product 1

HCID 178479224HCID 178479224, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1.0 M solution of borane in tetrahydrofuran (250 mL, 260 mmol.) was added slowly dropwise to a suspension of trans-4-(aminomethyl)cyclohexanecarboxylic acid (10.0 g, 64.0 mmol.) in tetrahydrofuran (250 mL). Gas evolution was observed. The reaction mixture was heated at reflux for 14 hours. The resulting solution was cooled to 0° C. and carefully treated dropwise with 1 N methanolic hydrochloric acid (250 mL). Gas evolution was observed. The white suspension obtained was stirred for 1 hour at 23° C. and subsequently concentrated. Methanol was added to the residue and the suspension was concentrated. This procedure was repeated twice to give trans-4-(Aminomethyl)cyclohexanemethanol hydrochloride (10.6 g, 93% yield) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 14 hours
  3. customThe white suspension obtained
  4. concentrationsubsequently concentrated
  5. additionMethanol was added to the residue
  6. concentrationthe suspension was concentrated

Sources & evidence

ORD record
ord-c435679d806244d58f5f7ddef198b09b
Source dataset
uspto-grants-2000_02
Patent number
US06022969

Reaction notes

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