Potassium Iodide → 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-(4,4-diphenylbutyl)piperazine (E)-2-butenedioate

HRID 275384Notes

Reaction equation

Cl.[C:2]1([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:25][CH2:26][C:27]1([CH2:41][CH3:42])[C:32]2[CH:33]=[C:34]([O:39][CH3:40])[C:35]([O:37][CH3:38])=[CH:36][C:31]=2[CH2:30][CH2:29][O:28]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:51]([OH:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([OH:56])=[O:55]>CN(C)C=O.C(O)C>[C:51]([OH:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([OH:56])=[O:55].[CH2:41]([C:27]1([CH2:26][CH2:25][N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][CH:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:17][CH2:16]2)[C:32]2[CH:33]=[C:34]([O:39][CH3:40])[C:35]([O:37][CH3:38])=[CH:36][C:31]=2[CH2:30][CH2:29][O:28]1)[CH3:42]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8 g of 1-(4,4-diphenylbutyl)piperazine hydrochloride, 8.4 g of known 1-(2-chloroethyl)-1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran, 5,6 g of potassium carbonate and 1 g of potassium iodide in 100 ml of dimethylformamide was heated at 100° C. for 3 h. After hydrolysis the mixture was extracted twice with ethyl acetate, dried and concentrated. The difumarate salt was prepared by adding 14.6 g of fumaric acid to a solution of the free base in ethanol, to give 4.2 g (35.6%) of 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-(4,4-diphenylbutyl)piperazine (E)-2-butenedioate (1:2) salt. mp 207.8° C.

Workup

customAfter hydrolysis the mixture
extractionwas extracted twice with ethyl acetate
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-249b47e655fc461abf0176b2f56b5d6e
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393759

Reaction notes

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