2-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine → 2-[[4-[(9-Fluorenyl)oxy]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

HRID 565671Notes

Reaction equation

HRID 565671 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[CH:17]1[C:29]2[CH:28]([O:30][CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1>>[CH:26]1[C:27]2[CH:28]([O:30][CH:31]3[CH2:36][CH2:35][N:34]([CH2:2][C:3]4([CH3:16])[CH2:7][C:6]5[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=5[O:4]4)[CH2:33][CH2:32]3)[C:29]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]=2[CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamineHCID 221109894-[(9-Fluorenyl)oxy]piperidine

Product 1

HCID 221110262-[[4-[(9-Fluorenyl)oxy]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamineYield 63%

Procedure

Using 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine and 4-[(9-fluorenyl)oxy]piperidine, the procedure of Example 1, presented below, was followed to provide 2-[[4-[(9-fluorenyl)oxy]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine. Yield 63%. A portion of the product was converted to the oxalate and recrystallized from ethanol to provide the title compound.

Sources & evidence

ORD record
ord-5985f33fb986473684dda719cd46c268
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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