HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 26968
Notes
Print preview

Reaction equation

HRID 26968 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 EtherSolvent
HCID 6212
Chloroform
Solvent

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-ef7f1125e2584476ae7a2f558029ebd1
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04151354

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes