N-Benzylnormechlorethamine → N-(Phenylmethyl)-1-piperidinesulfonamide

HRID 842240Notes

Reaction equation

C1(CN2CCC([S:18]([N:21]3[CH2:26][CH2:25][CH:24](OC4C=CC(OC(F)(F)F)=CC=4)[CH2:23][CH2:22]3)(=[O:20])=[O:19])(C(OC)=O)CC2)C=CC=CC=1.C=NS(=O)=O.C(=O)([O-])[O-].[K+].[K+].ClCC[N:53](CCCl)[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH2:54]([NH:53][S:18]([N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)(=[O:19])=[O:20])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Part G: Preparation of Methyl 1-(phenylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. To a solution of the methylene sulfonamide from part F (20.46 g, 51.5 mmol) in dimethylformamide (90 mL) was added potassium carbonate (21.3 g, 154.7 mmol), bis-(2-chloroethyl)benzyl amine (12.0 g, 51.5 mmol; and 18-Crown-6 (700 mg). The slurry was stirred at 60° C. After twenty four hr the reaction was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water three times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was recrystallized (methanol) to give the N-benzyl piperidine sulfonamide as a white solid (15 g, 52%).

Workup

concentrationAfter twenty four hr the reaction was concentrated in vacuo
washwashed with water three times, saturated sodium chloride solution
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was recrystallized (methanol)

Sources & evidence

ORD record: ord-e1117e905ffb44e4b3ee13d672fedef3
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372758B1

Reaction notes

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