Pyridine → 9-Chloromethyl-1-(2-trimethylsilanylethoxymethyl)-1,3,4,5-tetrahydrobenz[b]azepin-2-one

HRID 1712586Notes

Reaction equation

O[CH2:2][C:3]1[C:8]2[N:9]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:25])=O.N1C=CC=CC=1.[Cl-].[Li+]>CN(C)C=O>[Cl:25][CH2:2][C:3]1[C:8]2[N:9]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Analogously to Method E, 0.320 g of 9-hydroxymethyl-1-(2-trimethylsilanylethoxymethyl)-1,3,4,5-tetrahydrobenz[b]azepin-2-one is reacted with 0.100 ml of thionyl chloride and 0.080 ml of pyridine. The resulting intermediate is subsequently dissolved in 30 ml of N,N-dimethylformamide and the solution is admixed with 0.190 g of lithium chloride. The reaction mixture is subsequently stirred at 45° C. over 2 hours and subsequently concentrated by evaporation. The residue is taken up in 100 ml of tert-butyl methyl ether and the solution is washed with 80 ml of water. The aqueous phase is extracted with 60 ml of tert-butyl methyl ether and the combined organic phases are subsequently dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (1:1 EtOAc-heptane); Rt=5.38.

Workup

concentrationsubsequently concentrated by evaporation
washthe solution is washed with 80 ml of water
extractionThe aqueous phase is extracted with 60 ml of tert-butyl methyl ether
dry with materialthe combined organic phases are subsequently dried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-ab1dcffc718c456cb34a7e618c3467d0
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790715B2

Reaction notes

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