Diisopropylethylamine → 1-{3-[3-(3,4-Dimethoxyphenyl)4,5-dihydroisoxazol-5-yl]propyl}-4-(2-ethoxyphenyl)piperazine

HRID 1838290Notes

Reaction equation

HRID 1838290 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].Cl.[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH3:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(C(C)C)CC)(C)C>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:33]3[CH2:32][CH2:31][N:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[O:23][CH2:21][CH3:22])[CH2:35][CH2:34]3)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 128624181-(2-Ethoxyphenyl)piperazine HydrochlorideHCID 187533883-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal

Product 1

HCID 187533811-{3-[3-(3,4-Dimethoxyphenyl)4,5-dihydroisoxazol-5-yl]propyl}-4-(2-ethoxyphenyl)piperazineYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal (22.96 mg, 0.090 mmol), 1-(2-ethoxyphenyl)piperazine hydrochloride (20.0 mg, 0.082 mmol), molecular sieve (5 beads), NaBH(OAc)3 (52.4 mg, 0.247 mmol) and diisopropylethylamine (26.95 L, 0.082 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 22.9 mg (68.2%) of the target compound was obtained.

Sources & evidence

ORD record
ord-998072a6461f416fb67549f15927f4f5
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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