Diethylaminoethyl chloride → HCID 18357191, compound

HRID 1386999Notes

Reaction equation

HRID 1386999 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[C:18]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[O:19])=[CH:5][CH:4]=1.[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[C:18]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:28][CH2:27][N:29]([CH2:33][CH3:34])[CH2:30][CH3:31])=[CH:24][CH:25]=2)=[O:19])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 13364Diethylaminoethyl chlorideHCID 21182750HCID 21182750, compound

Product 1

HCID 18357191HCID 18357191, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By essentially following the procedure outlined in Example 3, part D, the title compound was prepared from 4-hydroxyphenyl 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl ketone (Example 28, Part A) and 2-diethylaminoethyl chloride in 86% yield. Flash chromatography [SiO2; gradient 1-4% of (1:1 TEA-MeOH) in EtOAc] gave the desired compound as a light oil.

Sources & evidence

ORD record
ord-49c6d397e2c44a65bc3936c008c783fc
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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