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(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene → (-)-cis-N-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-N'-(4-methoxyphenyl)isophthalamide

HRID 1862351
Notes
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Reaction equation

HRID 1862351 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:16][CH3:17].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](Cl)=[O:33])=[O:28])=[CH:22][CH:21]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:16][C:4]1[CH:5]=[C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[C:29]([C:27]([NH:26][C:23]3[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=3)=[O:28])[CH:30]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene2×HCID 186197543-(4-Methoxyphenylcarbamoyl)benzoyl chloride

Product 1

HCID 54028062(-)-cis-N-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-N'-(4-methoxyphenyl)isophthalamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×
HCID 8471
Triethylamine
Solvent

Procedure

4.0 g of (−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene (compound C2) are dissolved in 100 ml of methylene chloride and 5.0 ml of triethylamine. The solution is added dropwise at RT to 4.95 g of 3-(4-methoxyphenylcarbamoyl)benzoyl chloride in 50 ml of methylene chloride and the mixture is extracted with 100 ml each of water, 2N hydrochloric acid, satd. sodium hydrogencarbonate solution and water again after stirring overnight. The organic phase is dried using sodium sulfate and concentrated. The residue is taken up in petroleum ether (low)/ethyl acetate in the ratio 2/1, filtered off with suction and dried. 7.14 g of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with 100 ml each of water, 2N hydrochloric acid
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. filtrationfiltered off with suction
  5. customdried

Sources & evidence

ORD record
ord-d9727853c199434c9556e738d61b1a68
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06538005B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes