Triethylene Glycol → 2-(4-Chlorobenzyl)-1-[4-(4-fluorophenyl)butyl]perhydroazepine

HRID 27435

Reaction equation

HRID 27435 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]2[CH2:14][CH2:15][CH2:16][C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.O.NN.[OH-].[K+].C(O)COCCOCCO>C(OCC)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8172Triethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 233428532-(4-Chlorobenzyl)-1-[3-(4-fluorobenzoyl)propyl]perhydroazepine

Product 1

HCID 233428342-(4-Chlorobenzyl)-1-[4-(4-fluorophenyl)butyl]perhydroazepineYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Heat 0.5 g of the title compound of Example 39 with 1 ml of hydrazine hydrate, 0.5 g of potassium hydroxide and 5 ml of triglycol for 2 hours at 165°. Cool the resulting reaction mixture to ambient temperature. Mix the cooled reaction mixture with water and diethyl ether. Dry the ether phase over sodium sulfate and then concentrate it to obtain 0.3 g of the title compound as a viscous oil.

Workup

  1. temperatureCool
  2. customthe resulting reaction mixture to ambient temperature
  3. additionMix
  4. dry with materialDry the ether phase over sodium sulfate
  5. concentrationconcentrate it

Sources & evidence

ORD record
ord-263ae71c66374e658004a1b702d7a9d6
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Linked notes

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