Potassium Iodide → 1-[2-(3,4-dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(3,4-dimethoxyphenyl)piperidine fumarate

HRID 1110795Notes

Reaction equation

HRID 1110795 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.Cl.Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[C:32](=[O:35])([O-:34])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:8]([OH:17])(=[O:7])/[CH:9]=[CH:10]/[C:32]([OH:34])=[O:35].[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:4]([CH2:3][CH2:2][N:29]2[CH2:28][CH2:27][CH:26]([C:20]3[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=3)[CH2:31][CH2:30]2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyranHCID 200687584-(3,4-Dimethoxyphenyl)piperidine dihydrochloride

Product 1

HCID 221542831-[2-(3,4-dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(3,4-dimethoxyphenyl)piperidine fumarate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The B isomer of 1-[2-(3,4-dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(3,4-dimethoxyphenyl)piperidine fumarate is prepared by following the procedure of Example 16 but starting with the B isomer of 4-(2-bromoethyl)-3,4-dihydro-(2H)-benzopyran (1.5 g) and 4-(3,4-dimethoxyphenyl)piperidine dihydrochloride (1.78 g), followed by potassium carbonate (1.71 g) and potassium iodide (1.03 g) in 2-butanone (50 cc).

Sources & evidence

ORD record
ord-5576115eac87410e8aa3a77770961592
Source dataset
uspto-grants-1990_12
Patent number
US04977166

Reaction notes

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