Diethyl Ether → (R)-N-[8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]methanesulfonamide

HRID 1954782Notes

Reaction equation

HRID 1954782 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(OCC)C>N1C=CC=CC=1>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C@H:2]([NH:1][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54533693(R)-N-[8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]methanesulfonamideYield 63.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol) and triethylamine (0.50 mL, 3.6 mmol) in pyridine (15 mL) was added dropwise methanesulfonyl chloride (62 μL, 0.54 mmol). After the addition the reaction was allowed to stir at ambient temperature for 1 h. The solvent was evaporated in vacuo and the residue was purified on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (95:5:0.5) as the eluent. This gave, after crystalization from diethyl ether, 100 mg (63% yield) of the title compound as white crystals: mp 135-137° C.; [α]21D +22° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 323 (59, M+).

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-3910b815e51d42ec8e6967b6175ce416
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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