Hydrochloric Acid → HCID 131717839, compound

HRID 1614625Notes

Reaction equation

HRID 1614625 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH2:23]([Cl:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-:34].[Na+].[Na+].[ClH:39]>C(#N)C>[OH2:34].[ClH:32].[ClH:39].[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:23][CH:24]=[CH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:23][CH:24]=[CH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1.[ClH:32].[ClH:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 19771957N,alpha-bis(4-fluorophenyl)-4-piperidinemethanamine

Product 1

HCID 131717839HCID 131717839, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.41 g (11.3 mmol) of the N,α-bis(4-fluorophenyl)-4-piperidinemethanamine, 1.85 g (12.1 mmol) of cinnamyl chloride, and 2.00 g (19.0 mmol) of sodium carbonate in 300 mL of acetonitrile was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. An insoluble residue was removed by filtration. The CH2Cl2 solution was subjected to flash chromatography (silica gel, eluted with 3% CH3OH in CH2Cl2) to give an oil. This was converted to the HCl salt, and the salt was recrystallized from CH3OH/ether to give 1.83 g (32.7%) as a white crystalline solid, mp 239°-241° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between CH2Cl2 and dilute NaOH
  3. customAn insoluble residue was removed by filtration
  4. washThe CH2Cl2 solution was subjected to flash chromatography (silica gel, eluted with 3% CH3OH in CH2Cl2)
  5. customto give an oil
  6. customthe salt was recrystallized from CH3OH/ether
  7. customto give 1.83 g (32.7%) as a white crystalline solid, mp 239°-241° C.

Sources & evidence

ORD record
ord-9baaa2ac0e8d468dbd6c3b8637124e59
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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