Triethylamine → HCID 67922668, compound

HRID 2248618Notes

Reaction equation

HRID 2248618 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([N:9]([CH3:11])[CH3:10])[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[Cl:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:19][CH2:20][CH2:21][CH2:22][C:23]([N:5]1[CH2:6][CH2:7][C@H:8]([N:9]([CH3:10])[CH3:11])[C@H:3]([O:2][CH3:1])[CH2:4]1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 67922774HCID 67922774, compound

Product 1

HCID 67922668HCID 67922668, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (ice/bath) mixture of 7.9 parts of cis-3-methoxy-N,N-dimethyl-4-piperidinamine, 7 parts of N,N-diethylethanamine, 195 parts of dichloromethane were added dropwise 6.16 parts of 4-chlorobutanoyl chloride (temperature <5° C.). Upon completion, stirring was continued for 30 minutes. The organic layer was washed twice with a saturated sodium chloride solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 13.7 parts (100%) of cis-1-(4-chloro-1-oxobutyl)-3-methoxy-N,N-dimethyl-4-piperidinamine (int. 29).

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. washThe organic layer was washed twice with a saturated sodium chloride solution
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-3c6fc9dd2b4840a5b0fc0086c2a44e2c
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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