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

HRID 1648400Notes

Reaction equation

HRID 1648400 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.[NH2:35][C:36]([C:38]1[NH:39][C:40]2[C:45]([C:46]=1[CH2:47][C:48]([NH2:51])([CH3:50])[CH3:49])=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37]>>[ClH:20].[NH2:35][C:36]([C:38]1[NH:39][C:40]2[C:45]([C:46]=1[CH2:47][C:48]([NH:51][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])([CH3:49])[CH3:50])=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37]

Participants

4

Reactant 3

HCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamineHCID 152899972-[2-(2-Methylprop-1-yloxy)phenoxy]ethyl methanesulfonateHCID 15289998[2-(2-aminocarbonyl-1H-indol-3-yl)-1,1-dimethylethyl]amine

Product 1

HCID 19919935[2-(2-aminocarbonyl-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methylprop-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-(2-aminocarbonyl-1H-indol-3-yl)-1,1-dimethylethyl]amine, gave [2-(2-aminocarbonyl-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methylprop-1-yloxy)phenoxy]ethyl}amine hydrochloride, m.p. 154°-156° C.

Sources & evidence

ORD record
ord-84872f7bed2345c4a800625485d0db3a
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Reaction notes

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