1-(4-Fluorophenyl)piperazine → 1-(Biphenyl-2-ylmethyl)-4-(4-fluorophenyl)piperazine

HRID 334264Notes

Reaction equation

HRID 334264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]([CH:20]=O)=[CH:16][CH:17]=[CH:18][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C1(C2C=CC=CC=2)C=CC=CC=1CN1CCN(C2C=CC=CC=2)CC1>>[C:14]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 752601-(4-Fluorophenyl)piperazineHCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 716025231-(Biphenyl-2-ylmethyl)-4-phenylpiperazine

Product 1

HCID 716025261-(Biphenyl-2-ylmethyl)-4-(4-fluorophenyl)piperazine

Procedure

96 mg of the target compound (0.28 mmol, 34.0%) was obtained using 1-(4-fluorophenyl)piperazine (296 mg, 1.64 mmol), biphenyl-2-carbaldehyde (150 mg, 0.82 mmol) and NaBH(OAc)3 (529 mg, 2.46 mmol) according to the synthesis method of Compound 1.

Sources & evidence

ORD record
ord-581b726c078d4d77b17f366217d946fd
Source dataset
uspto-grants-2014_11
Patent number
US08883796B2

Reaction notes

Loading…