Diisopropylethylamine → HCID 10199883, compound

HRID 2086432Notes

Reaction equation

HRID 2086432 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][CH2:13][CH:14]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28]C[CH2:26][CH2:25]1.C([N:33](C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:33]([CH2:14][CH2:13][CH2:12][C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 14816484HCID 14816484, compoundHCID 23153645HCID 23153645, compound

Product 1

HCID 10199883HCID 10199883, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-(3-phenylisoxazol-5-yl)propanal (26.4 mg, 0.13 mmol), (2-chlorophenyl)piperidine HCl (25.5 mg, 0.11 mmol), and diisopropylethyl amine (19.0, 0.11 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (69.3 mg, 0.33 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 36.5 mg (87.7%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22 hr

Sources & evidence

ORD record
ord-14a1bd3a89a1461f8a738111df89f9ca
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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