4-[Bis(4-fluorophenyl)methyl]piperidine → HCID 20138030, compound

HRID 1253022Notes

Reaction equation

HRID 1253022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[Cl:22][CH2:23][CH2:24][CH:25]1[CH2:31][N:30]([CH3:32])[C:29](=[O:33])[C:28]2[CH:34]=[CH:35][CH:36]=[N:37][C:27]=2[CH2:26]1>C(O)C>[ClH:22].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH:25]3[CH2:31][N:30]([CH3:32])[C:29](=[O:33])[C:28]4[CH:34]=[CH:35][CH:36]=[N:37][C:27]=4[CH2:26]3)[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 14155950HCID 14155950, compound

Product 1

HCID 20138030HCID 20138030, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[Bis(4-fluorophenyl)methyl]piperidine and 8-(2-chloroethyl)-6,7,8,9-tetrahydro-6-methyl-5H-pyrido[3,2-c]azepin-5-one in ethanol are reacted by heating to reflux for about 20 hr. The solution is concentrated on a rotary evaporator and the residue is partitioned between aqueous dilute base and chloroform. The chloroform layer is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed by high pressure liquid chromatography using ethyl acetate and triethylamine over silica. After concentrating the desired fraction, the residue is converted to the hydrochloride salt in isopropyl alcohol using hydrogen chloride.

Workup

  1. temperatureby heating
  2. temperatureto reflux for about 20 hr
  3. concentrationThe solution is concentrated on a rotary evaporator
  4. customthe residue is partitioned between aqueous dilute base and chloroform
  5. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed by high pressure liquid chromatography
  8. concentrationAfter concentrating the desired fraction

Sources & evidence

ORD record
ord-ee35e2d89eb842159db6c1ce451f2b12
Source dataset
uspto-grants-1988_05
Patent number
US04746657

Reaction notes

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