Amantadine → 3-bromo-N,2-dimethyl-N-(tricyclo[3.3.1.13,7]dec-2-yl)benzamide

HRID 336612Notes

Reaction equation

HRID 336612 reaction equation
[C:1]12([NH2:11])CC3CC(CC(C3)C1)C2.[Br:12][C:13]1[C:14]([CH3:22])=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].[C:23]12(C(Cl)=O)[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2>>[Br:12][C:13]1[C:14]([CH3:22])=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([N:11]([CH3:1])[CH:24]1[CH:25]2[CH2:31][CH:29]3[CH2:28][CH:27]([CH2:32][CH:23]1[CH2:30]3)[CH2:26]2)=[O:17]

Participants

4

Reactant 3

HCID 2130AmantadineHCID 989151-Adamantanecarbonyl chlorideHCID 193678073-Bromo-2-methylbenzoyl chloride

Product 1

HCID 894986413-bromo-N,2-dimethyl-N-(tricyclo[3.3.1.13,7]dec-2-yl)benzamide

Procedure

The title compound was prepared by substituting N-adamantan-2-yl-N-methyl-amine for 1-adamantanamine and 3-bromo-2-methylbenzoyl chloride for 1-adamantanecarbonyl chloride in EXAMPLE 50A.

Sources & evidence

ORD record
ord-696e6b4402984b058db85639d3173f03
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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