Potassium Iodide → 1-[2-(3,4-Dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(4-hydroxy-3-methoxyphenyl)piperidine

HRID 1110799Notes

Reaction equation

HRID 1110799 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:14][CH3:15].Br[CH2:17][CH2:18][CH:19]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1.[I-].[K+]>CC(=O)CC>[O:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:19]([CH2:18][CH2:17][N:11]2[CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:14][CH3:15])[CH:4]=3)[CH2:13][CH2:12]2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyranHCID 221542522-Methoxy-4-(piperidin-4-yl)phenol

Product 1

HCID 221542261-[2-(3,4-Dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(4-hydroxy-3-methoxyphenyl)piperidine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-[2-(3,4-Dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(4-hydroxy-3-methoxyphenyl)piperidine is prepared by proceeding as in Example 48 but starting with 4-(4-hydroxy-3-methoxyphenyl)piperidine, 4-(2-bromoethyl)-3,4-dihydro-2H-benzopyran (0.49 g) and potassium iodide (0.5 g) in 2-butanone (35 cc).

Sources & evidence

ORD record
ord-a7936aebf7e4409cb6a49e00715abfc4
Source dataset
uspto-grants-1990_12
Patent number
US04977166

Reaction notes

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