1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) → HCID 20540365, compound

HRID 1065476Notes

Reaction equation

HRID 1065476 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][C:13]([CH2:14][CH:15]([CH3:17])[NH2:16])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:28][CH2:29][CH2:30][Cl:31])=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[ClH:31].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][CH:15]([NH:16][CH2:30][CH2:29][CH2:28][CH:27]([C:24]2[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=2)[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH3:17])=[CH:18][CH:19]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 81531DiisopropylethylamineHCID 20039876HCID 20039876, compound

Product 1

HCID 20540365HCID 20540365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 11.1 g of dl-p-benzyloxyamphetamine hydrochloride, 11.2 g of 4,4-di-(4-fluorophenyl)-butyl chloride, 10.34 g of diisopropyl-ethylamine and 50 ml of dimethylformamide is stirred at 100° for 60 hours. It is evaporated, the residue taken up in benzene and the solution washed three times with water. The organic layer is dried, evaporated, the residue taken up in diethyl ether and the solution acidified with hydrogen chloride in isopropanol to afford the dl-1-(p-benzyloxyphenyl)-2-[4,4-di-(4-fluorophenyl)-butylamino]-propane hydrochloride, melting at 130°-133°.

Workup

  1. customIt is evaporated
  2. washthe solution washed three times with water
  3. customThe organic layer is dried
  4. customevaporated

Sources & evidence

ORD record
ord-4a26b424c8af46fdbdac777b94ebe46a
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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