2-Bromopropane → 4-(Methoxymethyl)-N-phenyl-1-(propan-2-yl)piperidin-4-amine

HRID 1973835Notes

Reaction equation

HRID 1973835 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[CH3:5][O:6][CH2:7][C:8]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C>CN(C)C(=O)C>[CH3:5][O:6][CH2:7][C:8]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][N:11]([CH:2]([CH3:4])[CH3:3])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 8471TriethylamineHCID 183199324-(Methoxymethyl)-N-phenylpiperidin-4-amine

Product 1

HCID 233390404-(Methoxymethyl)-N-phenyl-1-(propan-2-yl)piperidin-4-amineYield 42.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 10 parts of 2-bromopropane, 9 parts of 4-(methoxymethyl)-N-phenyl-4-piperidinamine, 4.9 parts of N,N-diethylethanamine and 72 parts of N,N-dimethylacetamide is stirred and refluxed for 10.25 hours. After cooling, the formed N,N-diethylethanamine hydrobromide is filtered off and the filtrate is diluted with water. The product is extracted with methylbenzene. The extract is washed thoroughly with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 5.7 parts (42.6%) of 4-(methoxymethyl)-1-(1-methylethyl)-N-phenyl-4-piperidinamine as an oily residue.

Workup

  1. temperaturerefluxed for 10.25 hours
  2. temperatureAfter cooling
  3. filtrationthe formed N,N-diethylethanamine hydrobromide is filtered off
  4. additionthe filtrate is diluted with water
  5. extractionThe product is extracted with methylbenzene
  6. washThe extract is washed thoroughly with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (90:10) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

Sources & evidence

ORD record
ord-1dc3be036ff040dbbb9b6bb7e3e5c593
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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