Water → 3-Aminomethyl-1-diphenylmethylpiperidine

HRID 362907Notes

Reaction equation

HRID 362907 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([C:20]([NH2:22])=O)[CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].O>C1COCC1>[NH2:22][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:14]([CH:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 541420131-Diphenylmethylpiperidin-3-carboxamide

Product 1

HCID 543685343-Aminomethyl-1-diphenylmethylpiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Step 2): To a suspension of LiAlH4 (10 g, 263 mmol) in THF (100 ml) was added dropwise a solution of 1-diphenylmethylpiperidin-3-carboxamide (32 g, 109 mmol) in THF (130 ml) for 40 mins under stirring and cooling in an ice-bath. After the addition was complete, the mixture was refluxed for 2 hours and then cooled. To the resulting mixture, 15% NaOH aqueous solution and H2O were added dropwise in order, and the insoluble materials were filtered off. The filtrate was dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel to give 3-aminomethyl-1-diphenylmethylpiperidine as a colorless oil, 23 g (75.5%).

Workup

  1. temperaturecooling in an ice-bath
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperaturecooled
  5. filtrationthe insoluble materials were filtered off
  6. dry with materialThe filtrate was dried over MgSO4
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-80c3eb8df0044f8da9bea49b781d5fd2
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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