Methanol → [3-(2-Methyl-piperidin-1-yl)-propyl]-(5-phenyl-thiazol-2-ylmethyl)-amine

HRID 2220703Notes

Reaction equation

HRID 2220703 reaction equation
[C:1]1([C:7]2[S:11][C:10]([CH:12]=O)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[CH2:21][CH2:22][CH2:23][NH2:24].CO.[BH4-].[Na+]>ClCCl>[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[CH2:21][CH2:22][CH2:23][NH:24][CH2:12][C:10]1[S:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5202111-(3-Aminopropyl)-2-pipecolineHCID 4311764Sodium borohydrideHCID 139687965-Phenyl-1,3-thiazole-2-carbaldehyde

Product 1

HCID 59772997[3-(2-Methyl-piperidin-1-yl)-propyl]-(5-phenyl-thiazol-2-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental condition analogous to Example 18, from 5-phenyl-thiazole-2-carbaldehyde 0.16 g (1.05 mmol), 3-(2-methyl-piperidin-1-yl)-propylamine 0.2 g (1.05 mmol), in 5 mL of dry dichloromethane was added 2 g of molecular sieve. The reaction was stirred overnight at room temperature. The molecular sieve was filtered and dichloromethane was concentrated under vaccum. To the mixture was added 15 mL of dry methanol and sodium borohydride 0.04 g (1.155 mmol) was added at 0° C. after 30 minutes reaction goes to completion. The reaction was quenched with 2 mL acetone, 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 vaccum. Yield 0.3 g of compound.

Workup

  1. filtrationThe molecular sieve was filtered
  2. concentrationdichloromethane was concentrated under vaccum
  3. additionwas added at 0° C. after 30 minutes
  4. customreaction
  5. customThe reaction was quenched with 2 mL acetone, methanol
  6. concentrationwas concentrated under vacuum
  7. additionwas diluted with chloroform, organic layer
  8. washwas washed with 2 times 20 mL water
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under vaccum

Sources & evidence

ORD record
ord-a62376913e6b4a64968171e8843e4a8e
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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