Water → HCID 13361851, compound

HRID 2413487Notes

Reaction equation

HRID 2413487 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.CS(O[CH2:27][CH:28]1[CH2:32][O:31][C:30]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=2[Cl:46])([CH2:33][N:34]2[CH:38]=[CH:37][N:36]=[CH:35]2)[O:29]1)(=O)=O.[OH-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:46][C:40]1[CH:41]=[C:42]([Cl:45])[CH:43]=[CH:44][C:39]=1[C:30]1([CH2:33][N:34]2[CH:38]=[CH:37][N:36]=[CH:35]2)[O:29][CH:28]([CH2:27][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH2:8][N:7]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:6][CH2:5]3)[CH2:32][O:31]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 11177254HCID 11177254, compoundHCID 13361836HCID 13361836, compound

Product 1

HCID 13361851HCID 13361851, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

1.4 g of 6-hydroxy-2-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline, 2.1 g of (2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate and 0.3 g of tetrabutylammonium bromide are heated to reflux, with vigorous stirring, for 9 hours in a mixture of 40 ml of toluene and 10 ml of 50% strength sodium hydroxide solution. After cooling, 50 ml of water are added, and the organic phase is washed with water, dried over magnesium sulfate and evaporated in a rotary evaporator. The crude product is purified by column chromatography on silica gel using a mixture of ethyl acetate and methanol 19:1. 2.2 g of a colorless oil (76% of theory) which crystallizes on trituration with diethyl ether are obtained. Melting point: 121°-122°.

Workup

  1. temperatureAfter cooling
  2. washthe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in a rotary evaporator
  5. customThe crude product is purified by column chromatography on silica gel using
  6. additiona mixture of ethyl acetate and methanol 19:1
  7. custom2.2 g of a colorless oil (76% of theory) which crystallizes on trituration with diethyl ether
  8. customare obtained

Sources & evidence

ORD record
ord-90f79d8a558646a996fe732ab6ea816c
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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