1-Phenylpiperazine → HCID 18753378, compound

HRID 1838279Notes

Reaction equation

HRID 1838279 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH:14]([CH2:16][CH2:17][CH:18]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH:14]([CH2:16][CH2:17][CH2:18][N:29]3[CH2:30][CH2:31][N:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:27][CH2:28]3)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 187533883-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal

Product 1

HCID 18753378HCID 18753378, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal (36.3 mg, 0.135 mmol), 1-phenylpiperazine (20.0 mg, 0.123 mmol), molecular sieve (5 beads) and NaBH(OAc)3 (78.4 mg, 0.369 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 45.5 mg (90.1%) of the target compound was obtained.

Sources & evidence

ORD record
ord-4a2a078078e5498696ba60f4e54291c1
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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