Diisopropylethylamine → HCID 10277093, compound

HRID 2086433Notes

Reaction equation

HRID 2086433 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]2[CH:18]=[C:17]([CH2:19][CH2:20][CH:21]=O)[O:16][N:15]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35]C[CH2:33][CH2:32]1.C([N:40](C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][N:40]([CH2:21][CH2:20][CH2:19][C:17]2[O:16][N:15]=[C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)[CH:18]=2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22727349HCID 22727349, compoundHCID 23153645HCID 23153645, compound

Product 1

HCID 10277093HCID 10277093, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3-phenoxyphenyl)isoxazol-5-yl]propanal (40.8 mg, 0.14 mmol), (2-chlorophenyl)piperidine HCl (27.0 mg, 0.12 mmol), and diisopropylethyl amine (20.2, 0.12 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (73.8 mg, 0.35 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 22 hr and followed the same processes as in Example 1 to obtain 52.7 mg (95.6%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22 hr

Sources & evidence

ORD record
ord-c4e6a53b549c409d92374b8e979d041c
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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