3-Pyridinecarboxaldehyde → HCID 22941045, compound

HRID 342118Notes

Reaction equation

HRID 342118 reaction equation
[ClH:1].[CH2:2]([C@@H:6]1[NH:11][CH2:10][CH2:9][N:8]([C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:13])[CH2:7]1)[CH2:3][CH2:4][CH3:5].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[ClH:1].[ClH:1].[CH2:2]([C@H:6]1[CH2:7][N:8]([C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[O:13])[CH2:9][CH2:10][N:11]1[CH2:30][C:26]1[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22941049HCID 22941049, compound

Product 1

HCID 22941045HCID 22941045, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3(S)-Butyl-1-(1-naphthoyl)piperazine hydrochloride (0.200 g, 0.601 mmol) was reacted with pyridine-3-carboxaldehyde (0.062 mL, 0.661 mmol), sodium triacetoxyborohydride (0.321 g, 1.52 mmol), in dichloroethane (7 mL) at pH 5-6 in the presence of crushed molecular sieves as described in Example 8, Step A. The crude product was purified by silica gel chromatography with 30% acetone in hexane, followed by preparative HPLC (80-75% solvent A). After ion exchange, the title compound was isolated. FAB ms (m+1) 388. Anal. Calc. for C25H29N3O.2.3 HCl.0.95 H2O. C, 61.49; H, 6.85; N, 8.60. Found: C, 61.49; H, 7.01; N, 8.76.

Workup

  1. customThe crude product was purified by silica gel chromatography with 30% acetone in hexane

Sources & evidence

ORD record
ord-20b83a9a62814a1fa32ee07bbb4a37d9
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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