Hydroxylamine → HCID 66621670, compound

HRID 414910Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1([N:13]([CH3:15])[CH3:14])[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.[NH2:19]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1([N:13]([CH3:15])[CH3:14])[CH2:11][CH2:10][CH:9]([NH2:19])[CH2:8][CH2:7]1

Participants

Reactant 2

HCID 787Hydroxylamine

HCID 66621251HCID 66621251, compound

Product 1

HCID 66621670HCID 66621670, compound

Procedure

1.0 g 1-(3-chlorobenzyl)-N,N-dimethylcyclohexane-1,4-diamine, obtained as a cis/trans-mixture from 4-(3-chlorobenzyl)-4-dimethylaminocyclohexanone by reaction with hydroxylamine and reduction of the oxime obtained with lithium aluminium hydride (WO 02090317), dissolved in 5 ml DMF, was added to 0.74 g N-furan-2-yl-methylsuccinic acid at 0° C. and 0.59 ml N,N-diisopropylcarbodiimide followed by 0.5 g 1-hydroxybenzotriazole (HOBt) were added while stirring. After 3 hours in an ice bath, the mixture was stirred overnight at room temperature. For working up, one-molar sodium carbonate solution was added (pH>10) and the crude product (1.75 g) was isolated by extraction with ethyl acetate/THF (V:V=1:1), with subsequent drying over sodium sulphate and evaporation. The main fraction, obtained after column chromatography on silica gel (3.0×20 cm) with 250 ml diethyl ether, diethyl ether/methanol (V:V=4:1) and diethyl ether/methanol (V:V=1:1), of 718 mg was dissolved in 50 ml 2-butanone, 50 ml ethyl acetate and 2 ml methanol and, by adding 29 μl water and 200 μl chlorotrimethylsilane, converted into the corresponding hydrochloride of the N-[4-(3-chlorobenzyl)-4-dimethylaminocyclohexyl]-N′-furan-2-yl-methylsuccinic acid amide (648 mg of white solid, mp. 233-234.5° C.).

Sources & evidence

ORD record: ord-2ef59dd6e3614f7c9a0f56cfbf113edb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088763B2

Reaction notes

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