1-Phenylpiperidine → HCID 22727358, compound

HRID 2086440Notes

Reaction equation

HRID 2086440 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[C:9]([CH:11](C)[CH2:12][CH:13]=O)[O:8][N:7]=1.[C:16]1([N:22]2[CH2:27][CH2:26]C[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:42]([N:49]1CCNCC1)C1C=CC=CC=1>C(Cl)Cl>[C:16]1([N:22]2[CH2:27][CH2:26][N:49]([CH2:42][CH2:13][CH2:12][CH2:11][C:9]3[O:8][N:7]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 200381-PhenylpiperidineHCID 759941-BenzylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727329HCID 22727329, compound

Product 1

HCID 22727358HCID 22727358, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-(3-(2-thienyl)isoxazol-5-yl)butanal (23.5 mg, 0.106 mmol) and 1-phenylpiperidine (16.2, 0.106 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (67.4 mg, 0.318 mmol), cold acetic acid (7.3, 0.127 1mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 3 hr and followed the same processes as in Example 1 to obtain 36.9 mg (94.7%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 3 hr

Sources & evidence

ORD record
ord-77ec5df1d8a744ae95a834b3402de957
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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