Benzaldehyde → HCID 178521611, compound

HRID 239907Notes

Reaction equation

HRID 239907 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[C].[Pd].CO>[CH2:9]([N:1]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 178511715HCID 178511715, compound

Product 1

HCID 178521611HCID 178521611, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To methanol (1 kg) were added trans-4-aminocyclohexanol (200 g), benzaldehyde (553 g) and 10% palladium carbon (20 g), and the mixture was stirred under a hydrogen atmosphere at 60° C. for 24 hr. After cooling to room temperature, the catalyst was filtered off and washed with methanol (400 g). The filtrate and washings were added dropwise to water (2 kg) at 50° C. After cooling to room temperature, the precipitate was collected by filtration, washed with water:methanol=2:1 (volume ratio, 400 g) and dried under reduced pressure to give the title compound (472 g, yield 92%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe catalyst was filtered off
  3. washwashed with methanol (400 g)
  4. additionThe filtrate and washings were added dropwise to water (2 kg) at 50° C
  5. temperatureAfter cooling to room temperature
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialmethanol=2:1 (volume ratio, 400 g) and dried under reduced pressure

Sources & evidence

ORD record
ord-82068a661e784676a39d851f166a6adf
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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