Hydrochloric Acid → HCID 68673728, compound

HRID 1804727Notes

Reaction equation

HRID 1804727 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH:11]=O)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.[BH4-].[Na+].[ClH:29]>CO.[OH-].[Na+].CO>[ClH:29].[ClH:29].[ClH:29].[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][CH2:11][C:8]2[N:7]=[CH:6][C:5]3[O:4][CH2:3][CH2:2][O:1][C:10]=3[CH:9]=2)[CH2:15][CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4158521-Benzyl-4-piperidylamineHCID 4311764Sodium borohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde

Product 1

HCID 68673728HCID 68673728, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23721981Sodium hydroxide methanolSolvent

Procedure

A solution of 3.0 g of 2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-carbaldehyde and 3.4 g of 4-amino-1-benzylpiperidine in 30 mL of methanol was stirred for 50 minutes at room temperature, and a solution of 0.34 g of sodium borohydride in 30 mL of 0.01 mol/L sodium hydroxide/methanol was added dropwise thereto under ice cooling. The mixture was further stirred for 2 hours under ice cooling, 6 mL of concentrated hydrochloric acid was added dropwise thereto at 10° C. or lower and stirred for 1 hour 30 minutes. The solid product was obtained by filtration to give 6.8 g of 1-benzyl-N-(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)piperidin-4-amine trihydrochloride as a white solid.

Workup

  1. stirringat 10° C. or lower and stirred for 1 hour 30 minutes
  2. customThe solid product was obtained by filtration

Sources & evidence

ORD record
ord-0d14b781491a4978a5ab15c0bf2dad4d
Source dataset
uspto-grants-2013_01
Patent number
US08354426B2

Reaction notes

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