1-(2-Methoxyphenyl)piperazine → 1-(4'-Chlorobiphenyl-2-ylmethyl)-4-(2-methoxyphenyl)piperazine

HRID 334288Notes

Reaction equation

HRID 334288 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([CH:28]=O)=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=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>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28][N:12]2[CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10][CH2:11]2)=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 13936894'-Chlorobiphenyl-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 716025231-(Biphenyl-2-ylmethyl)-4-phenylpiperazine

Product 1

HCID 716026901-(4'-Chlorobiphenyl-2-ylmethyl)-4-(2-methoxyphenyl)piperazine

Procedure

215 mg of the target compound (0.55 mmol, 42.4%) was obtained using 1-(2-methoxyphenyl)piperazine (497 mg, 2.58 mmol), 4′-chlorobiphenyl-2-carbaldehyde (280 mg, 1.29 mmol) and NaBH(OAc)3 (832 mg, 3.87 mmol) according to the synthesis method of Compound 1.

Sources & evidence

ORD record
ord-df5479a52bb240b4b13fcdb2e3a5ec5f
Source dataset
uspto-grants-2014_11
Patent number
US08883796B2

Reaction notes

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