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

HRID 1648412Notes

Reaction equation

HRID 1648412 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.C1(C(C2C=CC=CC=2)[O:42][C:43]2[CH:51]=[C:50]3[C:46]([C:47]([CH2:52][C:53]([NH2:56])([CH3:55])[CH3:54])=[CH:48][NH:49]3)=[CH:45][CH:44]=2)C=CC=CC=1>>[ClH:20].[OH:42][C:43]1[CH:51]=[C:50]2[C:46]([C:47]([CH2:52][C:53]([NH:56][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])([CH3:54])[CH3:55])=[CH:48][NH:49]2)=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamineHCID 152899972-[2-(2-Methylprop-1-yloxy)phenoxy]ethyl methanesulfonateHCID 19919954[2-(6-diphenylmethyloxy-1H-indol-3-yl)-1,1-dimethylethyl]amine

Product 1

HCID 19919923[2-(6-hydroxy-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-(6-diphenylmethyloxy-1H-indol-3-yl)-1,1-dimethylethyl]amine and then removing the protective group, gave [2-(6-hydroxy-1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(2-methylprop-1-yloxy)phenoxy]ethyl}amine hydrochloride.

Workup

  1. customremoving the protective group

Sources & evidence

ORD record
ord-cb276466540a4f20943ad501126a32aa
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Reaction notes

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