Piperidine → 1-(4-Chlorobenzyl)-4-[{(4-isopropylphenylsulfonyl)glycyl}aminomethyl]piperidine

HRID 133598Notes

Reaction equation

C1CCNCC1.[CH:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)([CH3:9])[CH3:8].[Cl:20][C:21]1[CH:39]=[CH:38][C:24]([CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([CH2:32][NH:33][C:34](=[O:37])[CH2:35][NH2:36])[CH2:28][CH2:27]2)=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:39]=[CH:38][C:24]([CH2:25][N:26]2[CH2:27][CH2:28][CH:29]([CH2:32][NH:33][C:34](=[O:37])[CH2:35][NH:36][S:16]([C:13]3[CH:14]=[CH:15][C:10]([CH:7]([CH3:9])[CH3:8])=[CH:11][CH:12]=3)(=[O:18])=[O:17])[CH2:30][CH2:31]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A (piperidinomethyl)polystyrene resin (28 mg, 2.8 mmol/g) and 4-isopropylbenzenesulfonyl chloride (1.5 equivalents) were added to a chloroform (2 mL) solution of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine (14.8 mg, 0.05 mmol). The resulting mixture was stirred at 25° C. for 16 hours, then filtered and concentrated to thereby afford 1-(4-chlorobenzyl)-4-[[N-(4-isopropylphenylsulfonyl)glycyl]aminomethyl]piperidine (Compd. No. 869) (22.1 mg, 92%). The purity was determined by RPLC/MS (86%). ESI/MS m/e 478 (M++H, C24H32N3O3S).

Workup

filtrationfiltered
concentrationconcentrated to thereby afford 1-(4-chlorobenzyl)-4-[[N-(4-isopropylphenylsulfonyl)glycyl]aminomethyl]piperidine (Compd. No

Sources & evidence

ORD record: ord-26cd6a46834149cd9be198a7ae44bc5c
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390830B1

Reaction notes

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