(1,1'-Biphenyl)-2-carboxaldehyde → 1-(Biphenyl-2-ylmethyl)-4-(3-(trifluoromethyl)phenyl)piperazine

HRID 334284

Reaction equation

Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[C:18]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19]([CH:24]=O)=[CH:20][CH:21]=[CH:22][CH:23]=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:18]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][N:13]1[CH2:14][CH2:15][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:2])([F:16])[F:17])[CH:5]=2)[CH2:11][CH2:12]1

Participants

Reactant 4

HCID 121052(1,1'-Biphenyl)-2-carboxaldehyde

HCID 3084246TFMPP hydrochloride

HCID 5049666Sodium triacetoxyborohydride

HCID 716025231-(Biphenyl-2-ylmethyl)-4-phenylpiperazine

Product 1

HCID 716783451-(Biphenyl-2-ylmethyl)-4-(3-(trifluoromethyl)phenyl)piperazine

Procedure

19.2 mg of the target compound (0.05 mmol, 5.6%) was obtained using 1-(3-trifluoromethylphenyl)piperazine hydrochloride (437 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-2b6603d1447340f587d6b0dd73a23356
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883796B2

Linked notes

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