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

HRID 334274Notes

Reaction equation

HRID 334274 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:21]([CH:26]=O)=[CH:22][CH:23]=[CH:24][CH:25]=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:20]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][N:17]1[CH2:18][CH2:19][N:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 4

HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 129967051-(2-Phenoxyphenyl)piperazineHCID 716025231-(Biphenyl-2-ylmethyl)-4-phenylpiperazine

Product 1

HCID 716783421-(Biphenyl-2-ylmethyl)-4-(2-phenoxyphenyl)piperazine

Procedure

151 mg of the target compound (0.36 mmol, 64.9%) was obtained using 1-(2-phenoxyphenyl)piperazine (277 mg, 1.09 mmol), biphenyl-2-carbaldehyde (100 mg, 0.55 mmol) and NaBH(OAc)3 (355 mg, 1.65 mmol) according to the synthesis method of Compound 1.

Sources & evidence

ORD record
ord-08434493e8024b90b25e2171eb7158f6
Source dataset
uspto-grants-2014_11
Patent number
US08883796B2

Reaction notes

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