(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene → HCID 53795669, compound

HRID 1861723Notes

Reaction equation

HRID 1861723 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].[CH2:18]([N:20]1[N:24]=[N:23][C:22]([C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)=[N:21]1)[CH3:19]>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:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([C:22]3[N:23]=[N:24][N:20]([CH2:18][CH3:19])[N:21]=3)=[CH:26][CH:27]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene2×HCID 18621299HCID 18621299, compound

Product 1

HCID 53795669HCID 53795669, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3.0 g of (−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene (compound C2) are dissolved in 100 ml of methylene chloride and 3.0 ml of triethylamine. A solution of 3.0 g of 4-(2-ethyl-2-H-tetrazol-5-yl)benzoyl chloride in 50 ml of methylene chloride is added dropwise at RT and the mixture is extracted, after stirring for 2 h, with 100 ml each of water, 2N hydrochloric acid, satd. sodium hydrogencarbonate solution and water again. The organic phase is dried using sodium sulphate and concentrated. The residue is taken up in petroleum ether (low)/ethyl acetate in the ratio 2/1, filtered off with suction and dried. 5.2 g of the title compound of m.p. 188-192° C. are obtained.

Workup

  1. extractionthe mixture is extracted
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. filtrationfiltered off with suction
  5. customdried

Sources & evidence

ORD record
ord-8fbf437fd4dc473ba7c9a2392f080fe3
Source dataset
uspto-grants-2003_03
Patent number
US06534519B1

Reaction notes

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