Benzhydrylpiperazine → HCID 10301315, compound

HRID 1838293Notes

Reaction equation

HRID 1838293 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH:14]([CH2:16][CH2:17][CH2:18][CH:19]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:21]1([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH:27]([N:28]1[CH2:33][CH2:32][N:31]([CH2:19][CH2:18][CH2:17][CH2:16][CH:14]2[O:13][N:12]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:15]2)[CH2:30][CH2:29]1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 70048BenzhydrylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 18753384HCID 18753384, compound

Product 1

HCID 10301315HCID 10301315, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]butanal (31.0 mg, 0.111 mmol), 1-(diphenylmethyl)piperazine (25.6 mg, 0.101 mmol), molecular sieve (5 beads) and NaBH(OAc)3 (64.6 mg, 0.308 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 35.7 mg (68.4%) of the target compound was obtained.

Sources & evidence

ORD record
ord-437e04819d4e4b988def73b56f2f82b5
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

Loading…