{3-[3-(4-Chloro-phenyl)-benzo[d]isothiazol-6-yl]-prop-2-ynyl}-dimethyl-amine → {3-[3-(4-Chloro-phenyl)-benzo[d]isothiazol-6-yl]-propyl}-dimethyl-amine

HRID 347154Notes

Reaction equation

HRID 347154 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH2:19][N:20]([CH3:22])[CH3:21])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1>CCO.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22313967{3-[3-(4-Chloro-phenyl)-benzo[d]isothiazol-6-yl]-prop-2-ynyl}-dimethyl-amine

Product 1

HCID 22314100{3-[3-(4-Chloro-phenyl)-benzo[d]isothiazol-6-yl]-propyl}-dimethyl-amineYield 53%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

80 mg (0.25 mmol) {3-[3-(4-Chloro-phenyl)-benzo[d]isothiazol-6-yl]-prop-2-ynyl}-dimethyl-amine in 2 ml EtOH were hydrogenated in the presence of 20 mg PtO2. H2O, purification by flash silica gel column (CH2Cl2/MeOH 9:1) yielded 43 mg (53%) {3-[3-(4-Chloro-phenyl)-benzo[d]isothiazol-6-yl]-propyl}-dimethyl-amine as a colorless oil, MS: 331 (MH+, 1Cl).

Workup

  1. customH2O, purification by flash silica gel column (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-4f6080bbc7d8474c8bd7e64a69884d38
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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