3-Pyridinecarboxaldehyde → Hydrochloric Acid

HRID 1243306Notes

Reaction equation

HRID 1243306 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]3)[C:4]=2[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](C=O)[CH:23]=1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:24]4[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=4)[CH:17]3[CH3:30])[C:4]=2[CH:3]=1.[ClH:1]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21925663HCID 21925663, compound

Product 2

HCID 313Hydrochloric AcidHCID 69595526HCID 69595526, compound

Procedure

2-chloro-10-(1-pyridin-3-yl-methylpiperidin-3-yl)-10H-phenothiazine was prepared by treatment of 2-chloro-10-piperidin-3-yl-10H-phenothiazine (240 mg, 0.757 mmol) and 3-pyridinecarboxaldehyde (81 mg, 0.757 mmol) with sodium triacetoxyborohydride (224 mg, 1.06 mmol) to provide after treatment with ethereal HCl, the sub-titled compound (136 mg, 41%).

Sources & evidence

ORD record
ord-37eda6f863ec44b1b35c97811446d19d
Source dataset
uspto-grants-2006_10
Patent number
US07119089B2

Reaction notes

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