Potassium Hydroxide → HCID 21153172, compound

HRID 1447652Notes

Reaction equation

HRID 1447652 reaction equation
[CH3:1][N:2]([C@@H:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C@H:10]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:9]1)C(=O)OCC.[OH-].[K+]>C(O)CCC>[CH3:1][NH:2][C@@H:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C@H:10]([O:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 131711659HCID 131711659, compound

Product 1

HCID 21153172HCID 21153172, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 7.1 g of the product of Step A in 70 ml of n-butanol was mixed with stirring under nitrogen with 7 g of potassium hydroxide pastilles and the mixture was then refluxed for 17 hours. The mixture was evaporated to dryness and the residue was taken up in methylene chloride. The solution was washed with water and dried and evaporated to dryness to obtain 5.5 g of cis N-methyl-5-[4-trifluoromethylphenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in the form of an orange oil. The latter was dissolved in 30 ml of ethyl acetate and the solution was made acidic by addition of a solution of gaseous hydrogen chloride in ethyl acetate. Crystallized was effected and the mixture was vacuum filtered. The recovered product was washed with ethyl acetate and was dried to obtain 5.4 g of the hydrochloride of the cis product in the form of white crystals melting at ≈220° C.

Workup

  1. temperaturethe mixture was then refluxed for 17 hours
  2. customThe mixture was evaporated to dryness
  3. washThe solution was washed with water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5ee99326fe1841c186e5cd6adb671e42
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

Loading…