Methanol → HCID 59773014, compound

HRID 2220702Notes

Reaction equation

HRID 2220702 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[CH2:20][CH2:21][CH2:22][NH2:23].CO.[BH4-].[Na+]>ClCCl>[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[CH2:20][CH2:21][CH2:22][NH:23][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 62012-NaphthalenecarboxaldehydeHCID 5202111-(3-Aminopropyl)-2-pipecolineHCID 4311764Sodium borohydride

Product 1

HCID 59773014HCID 59773014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Naphtaldehyde 1 g (6.4 mmol), 3-(2-methyl-piperidin-1-yl)-propylamine 0.99 g (6.4 mmol), in 25 mL of dry dichloromethane was added 5 g of molecular sieve. The reaction was stirred overnight at room temperature. The molecular sieve was filtered and dichloromethane was concentrated under vacuum. To the mixture was added 15 mL of dry methanol and sodium borohydride 0.3 g (8 mmol) after 30 minutes reaction goes to completion, methanol was concentrated under vacuum, and was diluted with chloroform, organic layer was washed with 2 times 20 mL water, followed with brine. The organic layer was dried over magnesium sulfate and concentrated under vacuum. The compound was purified using silica gel chromatography elution, with 3.5% methanol in chloroform, yield 0.6 g oil.

Workup

  1. filtrationThe molecular sieve was filtered
  2. concentrationdichloromethane was concentrated under vacuum
  3. customreaction
  4. concentrationwas concentrated under vacuum
  5. additionwas diluted with chloroform, organic layer
  6. washwas washed with 2 times 20 mL water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe compound was purified
  10. washsilica gel chromatography elution

Sources & evidence

ORD record
ord-ada610ef824f4206a6bc54049f10bca9
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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