Water → 1-ethyl-N-[2-[bis(4-fluorophenyl)methoxy]ethyl]-3,4-dihydro-6,7-dimethoxyN-methyl-1H-2-benzopyran-1-ethanamine (+/-)-2,3-dihydroxybutanedioate

HRID 846680Notes

Reaction equation

HRID 846680 reaction equation
[CH2:1]([C:3]1([CH2:17][CH2:18][NH:19][CH3:20])[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[CH2:6][CH2:5][O:4]1)[CH3:2].ClCC[CH:24]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.[C:39](=[O:42])([O-:41])[O-:40].[K+].[K+].[OH2:45].[CH3:46]N(C)[CH:48]=[O:49]>>[OH:15][CH:10]([CH:48]([OH:49])[C:39]([OH:41])=[O:40])[C:11]([OH:13])=[O:45].[CH2:1]([C:3]1([CH2:17][CH2:18][N:19]([CH2:46][CH2:39][O:42][CH:24]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH3:20])[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[CH2:6][CH2:5][O:4]1)[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 197832871,1'-(3-Chloropropylidene)bis(4-fluorobenzene)HCID 198835851-ethyl-3,4-dihydro-6,7-dimethoxy-N-methyl-1H-2-benzopyran-1-ethanamine

Product 1

HCID 867460681-ethyl-N-[2-[bis(4-fluorophenyl)methoxy]ethyl]-3,4-dihydro-6,7-dimethoxyN-methyl-1H-2-benzopyran-1-ethanamine (+/-)-2,3-dihydroxybutanedioateYield 55%

Procedure

A mixture of 45 g of 1-ethyl-3,4-dihydro-6,7-dimethoxy-N-methyl-1H-2-benzopyran-1-ethanamine, 50 g of [1-(2-chloroethyl)]-bis-(4-fluorophenyl)methane, and 24.5 g of potassium carbonate in 500 ml of dimethylformamide was heated at 120°-140° C. for 2 h. The mixture was hydrolyzed with 1 l of water, extracted twice with 300 ml of diethylether and the organic phase was washed with water, dried and evaporated. The crude base was converted into the (±)-tartrate with (±)-tartaric acid in ethylacetate to give 60 g (55%) of 1-ethyl-N-[2-[bis(4-fluorophenyl)methoxy]ethyl]-3,4-dihydro-6,7-dimethoxyN-methyl-1H-2-benzopyran-1-ethanamine (±)-2,3-dihydroxybutanedioate (1:1) salt. m.p. 118.5° C.

Workup

  1. temperaturewas heated at 120°-140° C. for 2 h
  2. extractionextracted twice with 300 ml of diethylether
  3. washthe organic phase was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ba4ece54a70b460f97042f7e184cfe0b
Source dataset
uspto-grants-1992_08
Patent number
US05137911

Reaction notes

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