Water → HCID 86747158, compound

HRID 275396Notes

Reaction equation

HRID 275396 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:20][CH3:21])=[CH:5][C:6]2[CH:11]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:10][CH2:9][CH2:8][C:7]=2[CH:19]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[CH2:30][CH2:31][CH2:32]Cl)=[CH:25][CH:24]=1.[C:41](=[O:44])([O-:43])[O-].[K+].[K+].[OH2:47]>CN(C)C=O>[C:9]([OH:10])(=[O:47])/[CH:8]=[CH:7]\[C:41]([OH:43])=[O:44].[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[CH2:30][CH2:31][CH2:32][N:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH:11]3[C:6]4[CH:5]=[C:4]([O:20][CH3:21])[C:3]([O:2][CH3:1])=[CH:19][C:7]=4[CH2:8][CH2:9][O:10]3)[CH2:14][CH2:15]2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 20087955HCID 20087955, compound

Product 1

HCID 86747158HCID 86747158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.2 g of (+)-1-[(3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)methyl]-piperazine were reacted with 13.6 g of 1,1-bis(4-fluorophenyl)-4-chlorobutane and 8 g of potassium carbonate in 100 ml of dimethyl formamide for 2 h. Water was added to the mixture and after work up, the dimaleate was prepared as previously described to obtain 11.4 g of (+)-1-[4,4-bis(4-fluorophenyl)butyl]-4-[(3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1yl)methyl]piperazine (Z)-2-butenedioate (1:2) salt. mp 200° C. The free base has an optical rotation of [α]D20 =+38.5° (c=1, methanol).

Sources & evidence

ORD record
ord-9cdb90e9f24446c19fdff5309133583c
Source dataset
uspto-grants-1995_02
Patent number
US05393759

Reaction notes

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