4-Chlorobenzoyl chloride → 4-Chloro-N-[[2-[2-(4-morpholinyl)ethoxy]phenyl]methyl]-N-(2-phenylethyl)benzamide, hydrochloride salt

HRID 1112446Notes

Reaction equation

HRID 1112446 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>C(Cl)(Cl)Cl.CCOCC>[ClH:26].[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:17]([CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 21322749N-[[2-[2-(4-Morpholinyl)ethoxy]phenyl]methyl]benzeneethanamine

Product 1

HCID 1317113154-Chloro-N-[[2-[2-(4-morpholinyl)ethoxy]phenyl]methyl]-N-(2-phenylethyl)benzamide, hydrochloride saltYield 168.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

N-[[2-[2-(4-Morpholinyl)ethoxy]phenyl]methyl]benzeneethanamine (40 g) and 22 g of p-chlorobenzoyl chloride are reacted in 600 ml of chloroform following the procedure described in Example 1C. The residue from the chloroform evaporation is first triturated with ether (evaporation repeated) and then with 400 ml of warm acetone to give a crystalline product. After diluting with 500 ml of ether and cooling for about 16 hours, the solid is filtered under nitrogen, washed with ether and dried in vacuo to yield 54.7 g of material, melting point 147°-149° C (sintering at 145° C). Crystallization from 250 ml of warm methanol-1750 ml ether yield 52.9 g of the title compound, melting point 147°-149° C.

Workup

  1. customThe residue from the chloroform evaporation
  2. customis first triturated with ether (evaporation repeated)
  3. customwith 400 ml of warm acetone to give a crystalline product
  4. temperaturecooling for about 16 hours
  5. filtrationthe solid is filtered under nitrogen
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-641cfdab69b849f3b49f0617c7595ae5
Source dataset
uspto-grants-1978_10
Patent number
US04122255

Reaction notes

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