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

HRID 2187413Notes

Reaction equation

HRID 2187413 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 crystallization 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-c60aca4fa44c4ad7b00b03cb5207e622
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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