tert-butyl N-(3-bromopropyl)carbamate → tert-butyl 3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate

HRID 2088089Notes

Reaction equation

HRID 2088089 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH:13]1[CH2:18][CH:17]=[C:16]([C:19]2[CH:20]=[C:21]([NH:25][C:26](=[O:28])[CH3:27])[CH:22]=[CH:23][CH:24]=2)[CH2:15][CH2:14]1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O1CCOCC1>[C:26]([NH:25][C:21]1[CH:20]=[C:19]([C:16]2[CH2:17][CH2:18][N:13]([CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:14][CH:15]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 21957228N-(3-(1,2,3,6-Tetrahydropyridin-4-yl)phenyl)acetamide

Product 1

HCID 21957172tert-butyl 3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

The reaction of tert-butyl N-(3-bromopropyl)carbamate and N-[3-(1,2,3,6-tetrahydro-4-pyridinyl)phenyl]acetamide in refluxing dioxane with catalytic Bu4NI and base as described in Scheme A gave tert-butyl 3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate. Deprotection of the BOC group using HCl in dioxane followed by basification (pH 11-12) gave the desired product.

Sources & evidence

ORD record
ord-dba1637ede634042b9668737f089e5cd
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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