5-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamine → [2-(6-fluoro-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methyl-prop-1-yloxy)phenoxy]ethyl}amine hydrochloride

HRID 1648402Notes

Reaction equation

HRID 1648402 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH:17]([CH3:19])[CH3:18])(=O)=O.[Cl:20]C1C=C2C(=CC=1)NC=C2CC(N)(C)C.[F:35][C:36]1[CH:44]=[C:43]2[C:39]([C:40]([CH2:45][C:46]([NH2:49])([CH3:48])[CH3:47])=[CH:41][NH:42]2)=[CH:38][CH:37]=1>>[ClH:20].[F:35][C:36]1[CH:44]=[C:43]2[C:39]([C:40]([CH2:45][C:46]([NH:49][CH2:6][CH2:7][O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH2:16][CH:17]([CH3:18])[CH3:19])([CH3:47])[CH3:48])=[CH:41][NH:42]2)=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamineHCID 152899972-[2-(2-Methylprop-1-yloxy)phenoxy]ethyl methanesulfonateHCID 199199781-(6-fluoro-1H-indol-3-yl)-2-methylpropan-2-amine

Product 1

HCID 19919948[2-(6-fluoro-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methyl-prop-1-yloxy)phenoxy]ethyl}amine hydrochloride

Procedure

Proceeding as an Example 3, but replacing 2-[2-(cyclopropylmethyloxy)phenoxy]ethyl methanesulfonate with 2-[2-(2-methylprop-1-yloxy)phenoxy]ethyl methanesulfonate and [2-(5-chloro-1H-indol-3-yl)-1,1-dimethylethyl]amine with [2- (6-fluoro-1H-indol-3-yl)-1,1-dimethylethyl]amine, gave [2-(6-fluoro-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methyl-prop-1-yloxy)phenoxy]ethyl}amine hydrochloride, m.p. 135°-137° C.

Sources & evidence

ORD record
ord-cc96e3404e7b43729056680b6d7c151d
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Reaction notes

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