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

HRID 1648404Notes

Reaction equation

HRID 1648404 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.[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40]([CH3:45])=[C:39]2[CH2:46][C:47]([NH2:50])([CH3:49])[CH3:48]>>[ClH:20].[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40]([CH3:45])=[C:39]2[CH2:46][C:47]([NH:50][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]([CH3:18])[CH3:19])([CH3:48])[CH3:49]

Participants

4

Reactant 3

HCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamineHCID 15289632[2-(5-chloro-2-methyl-1H-indol-3-yl)-1,1-dimethylethyl]amineHCID 152899972-[2-(2-Methylprop-1-yloxy)phenoxy]ethyl methanesulfonate

Product 1

HCID 19919930[2-(5-chloro-2-methyl-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methylprop-1-yloxy)phenoxy]ethyl}amine hydrochloride

Procedure

Proceeding as in 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-(5-chloro-2-methyl-1H-indol-3-yl)-1,1-dimethylethyl]amine, gave [2-(5-chloro-2-methyl-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methylprop-1-yloxy)phenoxy]ethyl}amine hydrochloride, m.p. 202°-204° C.

Sources & evidence

ORD record
ord-5277ee11a2a045eab27a8f8d6304c4f9
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Reaction notes

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