Methanesulfonyl chloride → (S)-2-Benzyl-4-(3-cyclopentyloxy4-methoxy-phenyl)-1-methanesulfonyl-piperazine

HRID 1171904Notes

Reaction equation

HRID 1171904 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[S:29]([CH3:28])(=[O:31])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Product 1

HCID 23627630(S)-2-Benzyl-4-(3-cyclopentyloxy4-methoxy-phenyl)-1-methanesulfonyl-piperazineYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the bis-hydrochloride salt of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (50 mg, 0.114 mmol) in pyridine (1 mL) was treated with methanesulfonyl chloride (26 μL, 0.341 mmol) and stirred at room temperature for 16 h. The reaction mixture was evaporated and partitioned between EtOAc (2 mL) and a saturated aqueous NaHCO3 solution (2 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 30% then 40% EtOAc/hexane as eluant to afford product as an oil (46 mg, 91%). 1H NMR (CDCl3) 1.60-1.62 (M, 2H), 1.84-1.87 (m, 4H), 1.90-2.04 (m, 2H), 2.55 (s, 3H), 2.76-2.80 (m, 2H), 3.19-3.56 (m, 5H), 3.77 (m, 1H), 3.80 (s, 3H), 4.30 (br t, 1H), 4.71 (m, 1H), 6.42 (br d, J=8.1, 1H), 6.48 (br s, 1H), 6.78 (d, J=8.6, 1H), 7.23-7.36 (m, 5H). LC/MS 7.25 min, [M+1]+ 445.

Workup

  1. customThe reaction mixture was evaporated
  2. custompartitioned between EtOAc (2 mL)
  3. customThe organic component was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customwas purified by silica gel flash chromatography with 30%

Sources & evidence

ORD record
ord-3baaa29e849f4e918a391abab3d9a392
Source dataset
uspto-grants-2010_11
Patent number
US07829713B2

Reaction notes

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