Diisopropylethylamine → HCID 18753379, compound

HRID 1838298Notes

Reaction equation

HRID 1838298 reaction equation
[C:1]1([C:7]2[CH2:11][CH:10]([CH2:12][CH2:13][CH2:14][CH:15]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH:27]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:10]1[O:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 187533924-(3-Phenyl-4,5-dihydroisoxazol-5-yl)butanal

Product 1

HCID 18753379HCID 18753379, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Phenyl-4,5-dihydroisoxazol-5-yl)butanal (20.9 mg, 0.096 mmol), 1-(2-methoxyphenyl)piperazine hydrochloride (20.0 mg, 0.087 mmol), molecular sieve (5 beads), NaBH(OAc)3 (55.6 mg, 0.262 mmol) and diisopropylethylamine (26.9 L, 0.087 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 25.5 mg (69.2%) of the target compound was obtained.

Sources & evidence

ORD record
ord-b67fbb2b64204373a7a1ea2a91903af9
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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