1-Benzyl-4-piperidylamine → HCID 67242287, compound

HRID 2422091Notes

Reaction equation

HRID 2422091 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([N:19]1[C:23](=[O:24])[C:22](Cl)=[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:20]1(=[O:33])=[O:32])([CH3:18])([CH3:17])[CH3:16]>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[C:23](=[O:24])[N:19]([C:15]([CH3:17])([CH3:16])[CH3:18])[S:20](=[O:33])(=[O:32])[C:21]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4158521-Benzyl-4-piperidylamineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 67242287HCID 67242287, compoundYield 58%

Procedure

The title compound was prepared as described for Example 24 from 1 equivalent 1-benzylpiperidine-4-amine, 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 1 equivalent TEA with a reaction time of 30 mins. The residue was purified by silica gel column chromatography (Horizons Biotage) using 35% EtOAc in petroleum ether 40-60° C. as eluent to give the title compound (0.132 g, 58%) as a solid. 1H NMR (500 MHz CDCl3): δ 7.54-7.7.47 (m, 2H), 7.46-7.42 (m, 3H), 7.31-7.26 (m, 2H), 7.26-7.21 (m, 3H), 5.20 (d, 1H), 3.35 (s, 2H), 2.99-2.90 (m, 1H), 2.67-2.62 (m, 2H), 1.74 (s, 9H), 1.71-1.56 (m, 4H), 1.44-1.33 (m, 2H); 13C NMR (125 MHz CDCl3): δ 159.9, 138.5, 134.2, 131.8, 129.9, 129.1, 128.8, 128.4, 127.3, 125.4, 106.7, 62.9, 61.7, 51.9, 50.3, 32.6, 27.8; Mass spectrum: M+H+ 454.

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by silica gel column chromatography (Horizons Biotage)
  3. custom35% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-8c0b5ed518754b698ab62d34299b2ba6
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

Loading…