Triethylamine → 1-[5-(Benzyloxy)pyridin-2-yl]-4-(methanesulfonyl)piperazine

HRID 1723811Notes

Reaction equation

HRID 1723811 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:17][CH2:16]2)=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222215041-[5-(Benzyloxy)pyridin-2-yl]piperazine

Product 1

HCID 688458821-[5-(Benzyloxy)pyridin-2-yl]-4-(methanesulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 1-[5-(benzyloxy)pyridin-2-yl]piperazine (104 g, 278 mmol) in CH2Cl2 (1.1L) at 0° C. was treated sequentially with triethylamine (94 mL, 672 mmol) and methanesulfonyl chloride (31 mL, 400 mmol). The reaction was brought to room temperature and stirred for 3 hour. The reaction was then diluted with DCM (3L) and washed with water (1L), HCl (0.5 M, 2×800 mL) and sat. NaHCO3 (800 mL), back-extracting with DCM (500 mL). The combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give 1-[5-(benzyloxy)pyridin-2-yl]-4-(methylsulfonyl)piperazine as a dark liquor (120 g, 278 mmol @ 81 wt %, 100%).

Workup

  1. customwas brought to room temperature
  2. washwashed with water (1L), HCl (0.5 M, 2×800 mL) and sat. NaHCO3 (800 mL)
  3. extractionback-extracting with DCM (500 mL)
  4. dry with materialThe combined organic extracts were then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20d7939396b64d2bb6c0c0ed8dc75f4a
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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