Dichloromethane → HCID 10271219, compound

HRID 2086395Notes

Reaction equation

HRID 2086395 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH:15]=O)[O:10][N:9]=1.[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)[Cl:44]>>[Cl:44][C:6]1[CH:5]=[CH:4][C:3]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][N:26]3[CH2:27][CH2:28][N:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:24][CH2:25]3)[O:10][N:9]=2)=[CH:2][CH:7]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 70961-PhenylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727330HCID 22727330, compound

Product 1

HCID 10271219HCID 10271219, compoundYield 70%

Procedure

About 2 min after dissolving 3-[3-(2-chlorophenyl)isoxazol-5-yl]propanal (15.8 mg, 0.09 mmol) and 1-phenylpiperazine (13.4, 0.07 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (42.6 mg, 0.2 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 36 hr and followed the same processes as in Example 1 to obtain 17.9 mg (70.0%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 36 hr

Sources & evidence

ORD record
ord-ea0b6afb3a9e40c9aa03af936956af5c
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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