Tetrahydrofuran → 1-(Cyclopropylmethyl)-4-(2',2'-bis (4"-Fluorophenyl)-2-hydroxyethyl)piperidine

HRID 5140Notes

Reaction equation

HRID 5140 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([CH2:11]OC3C=CC(F)=CC=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1.[O:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:1]1([CH2:4][N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][C:33]([C:32]3[CH:23]=[CH:22][C:21]([F:20])=[CH:30][CH:31]=3)([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)[OH:29])[CH2:9][CH2:10]2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 100156311-Cyclopropylmethyl-4-(4-fluoro-phenoxymethyl)-piperidineHCID 178418676HCID 178418676, compound

Product 1

HCID 538117721-(Cyclopropylmethyl)-4-(2',2'-bis (4"-Fluorophenyl)-2-hydroxyethyl)piperidine

Procedure

Following the procedure described for Example 547, the compound of Example 429 (1.0 g, 3.6 mmol) was reacted a solution of 4-fluorophenylmagnesium bromide in tetrahydrofuran (1.0M, 9 mL, 9 mmol) to give the title compound, a solid (1.1 g): mp 119°-121° C.; Anal.: Calcd for C23H27F2NO.0.5H2O: C, 72.60, H, 7.41, N, 3.68, F, 9.99; Found: C, 72.89, 72.84, H, 7.14, 7.21, N, 3.29, 3.24, F, 9.82, 9.67.

Sources & evidence

ORD record
ord-a1afae4c809643d59843e94bfd9a4e3d
Source dataset
uspto-grants-1993_09
Patent number
US05243048

Reaction notes

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