2-(Dimethylamino)ethanol → HCID 86757214, compound

HRID 1387064Notes

Reaction equation

HRID 1387064 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([C:26]3[CH:31]=[CH:30][C:29](F)=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][OH:37].C(Cl)(Cl)Cl.[CH3:43][OH:44].[NH4+].[OH-:46]>>[C:24]([OH:25])(=[O:37])[C:43]([OH:46])=[O:44].[C:36]([OH:37])(=[O:8])[C:43]([OH:46])=[O:44].[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:37][CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 107182054-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketoneHCID 21873181Chloroform methanol ammonium hydroxide

Product 1

HCID 86757214HCID 86757214, compoundYield 55%

Procedure

The title compound was prepared from 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (Example 132, Part A) and 2-(dimethylamino)ethanol in 55% yield after radial chromatography (SiO2; gradient of 98:1.5:0.5 to 95:4:1 CHCl3—MeOH—NH4OH) by essentially following the procedure described in Example 132, Part B.

Sources & evidence

ORD record
ord-d91d3e8f3f544f8a874b983da8ad3612
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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