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Chlorobenzene → HCID 21398521, compound

HRID 1731012
Notes
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Reaction equation

HRID 1731012 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH:9]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C[O-].[Na+].ClC1C=CC=CC=1.Cl[CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40]>CO>[CH2:37]([N:38]([CH2:41][CH3:42])[CH2:39][CH2:40][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH:9]2[C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[CH:4][CH:3]=1)[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 13364Diethylaminoethyl chlorideHCID 10942334Sodium MethoxideHCID 213984754-[2-(4-Chlorophenyl)-3,4-dihydro-1(2H)-quinolinyl]phenol

Product 1

HCID 21398521HCID 21398521, compound

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A procedure was followed similar to that described in Example 1 but using 18 g. 1-(4-hydroxyphenyl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoline, 3.8 g. sodium methoxide, 160 ml. chlorobenzene, 15 ml. dry methanol and 8.8 g. N-(2-chloroethyl) diethylamine. The crude material was chromatographed on 700 g. activated magnesium silicate (60-100 mesh) using benzene, benzene containing increasing amounts of ether, and ether as eluants and there was thus eluted with 7 - 50% ether in benzene and with ether 15 g. 1-{4-[2-(diethylamino)ethoxy]phenyl}-2-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoline which was converted to the cyclohexanesulfamate salt; m.p. 161°-163°C. (isopropyl alcohol).

Workup

  1. customThe crude material was chromatographed on 700 g
  2. temperatureincreasing amounts of ether, and ether as eluants
  3. washthere was thus eluted with 7 - 50% ether in benzene and with ether 15 g

Sources & evidence

ORD record
ord-c09cd2c6e72b45a59d365ba79df79a63
Source dataset
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03994902

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes