Triethylamine → HCID 53308222, compound

HRID 1846612Notes

Reaction equation

HRID 1846612 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:22])[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([NH:22][C:4]1[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 67341275HCID 67341275, compound

Product 1

HCID 53308222HCID 53308222, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.075 g (0.25 mmol) of 5′-methyl-4-(2-piperidin-1-yl-ethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-ylamine in methylene chloride (5 mL) is added 0.050 mL (0.30 mmol) of triethylamine followed by 0.044 g (0.25 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred overnight at room temperature then purified by preparative reverse phase HPLC to give 0.033 g (30%) of the title compound (3) as a white solid. [M+H]+=441.3.

Workup

  1. customthen purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-9ae2b2d222d844e6ab5babe73c92ef0b
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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