(1,1'-Biphenyl)-2-carboxaldehyde → 1-(Biphenyl-2-ylmethyl)-4-(4-chlorophenyl)piperazine

HRID 334267Notes

Reaction equation

HRID 334267 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:15]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]([CH:21]=O)=[CH:17][CH:18]=[CH:19][CH:20]=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:15]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][N:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 4

HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 30847201-(4-Chlorophenyl)piperazine HydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 716025231-(Biphenyl-2-ylmethyl)-4-phenylpiperazine

Product 1

HCID 716025821-(Biphenyl-2-ylmethyl)-4-(4-chlorophenyl)piperazine

Procedure

20 mg of the target compound (0.06 mmol, 7.3%) was obtained using 1-(4-chlorophenyl)piperazine hydrochloride (382 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-0368ddab7a6b4dc9ba6579dacd37221a
Source dataset
uspto-grants-2014_11
Patent number
US08883796B2

Reaction notes

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