Benzhydrylpiperazine → HCID 10162344, compound

HRID 1838291Notes

Reaction equation

HRID 1838291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][CH2:14][CH2:15][CH:16]=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.[C:18]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH:24]([N:25]1[CH2:30][CH2:29][N:28]([CH2:16][CH2:15][CH2:14][CH2:13][CH:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:12]2)[CH2:27][CH2:26]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 70048BenzhydrylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 18753377HCID 18753377, compound

Product 1

HCID 10162344HCID 10162344, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(4-Fluorophenyl)-4,5-dihydroisoxazol-5-yl]butanal (27.0 mg, 0.114 mmol), 1-(diphenylmethyl)piperazine (26.3 mg, 0.104 mmol), molecular sieve (5 beads) and NaBH(OAc)3 (66.3 mg, 0.313 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 32.0 mg (65.1%) of the target compound was obtained.

Sources & evidence

ORD record
ord-43c233eefe6e4bfc856623a04598e868
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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