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

HRID 1648403Notes

Reaction equation

HRID 1648403 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.[CH3:35][C:36]1[NH:37][C:38]2[C:43]([C:44]=1[CH2:45][C:46]([NH2:49])([CH3:48])[CH3:47])=[CH:42][C:41]([CH3:50])=[CH:40][CH:39]=2>>[ClH:20].[CH3:35][C:36]1[NH:37][C:38]2[C:43]([C:44]=1[CH2:45][C:46]([NH:49][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])([CH3:47])[CH3:48])=[CH:42][C:41]([CH3:50])=[CH:40][CH:39]=2

Participants

4

Reactant 3

HCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamineHCID 152899972-[2-(2-Methylprop-1-yloxy)phenoxy]ethyl methanesulfonateHCID 15289999[2-(2,5-dimethyl-1H-indol-3-yl)-1,1-dimethylethyl]amine

Product 1

HCID 19919925[2-(2,5-dimethyl-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-(2,5-dimethyl-1H-indol-3-yl)-1,1-dimethylethyl]amine, gave [2-(2,5-dimethyl-1H- indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methylprop-1-yloxy)phenoxy]ethyl}amine hydrochloride, m.p. 216°-218° C.

Sources & evidence

ORD record
ord-3e8b79fbe37b47aebbb2d5651f47eebc
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Reaction notes

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