Sodium Carbonate → HCID 131717841, compound

HRID 1614627Notes

Reaction equation

HRID 1614627 reaction equation
O.[ClH:2].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[O:25]([CH2:32][CH2:33][CH2:34]Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[OH2:25].[ClH:2].[ClH:2].[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH:11]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:34][CH2:33][CH2:32][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:14][CH2:13]2)=[CH:8][CH:9]=1.[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH:11]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:34][CH2:33][CH2:32][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:14][CH2:13]2)=[CH:8][CH:9]=1.[ClH:2].[ClH:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 19771956HCID 19771956, compound

Product 1

HCID 131717841HCID 131717841, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.92 g (10.5 mmol) of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine hydrochloride hydrate, 2.77 g (13.0 mmol) of 3-phenoxy propyl bromide, 3.80 g (36.0 mmol) of sodium carbonate, and 0.61 g (3.7 mmol) of KI in 400 mL of 1-butanol was heated at reflux for 69 h. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo. The residue was subjected to flash column chromatography (silica gel, elution with 1 to 3% CH3OH in CH2Cl2) to give the free base of the title compound. This was converted to the HCl salt, and the salt was recrystallized from CH3OH/ether to give 3.59 g (65.9%) of the title compound as a white crystalline solid, mp 222°-226° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 69 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between CH2Cl2 and dilute NaOH
  5. dry with materialThe CH2Cl2 solution was dried (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. washThe residue was subjected to flash column chromatography (silica gel, elution with 1 to 3% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-5580d43b5bc0466296946b998c93cbb8
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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