Triethylamine → HCID 89938217, compound

HRID 2200356Notes

Reaction equation

HRID 2200356 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:18])[CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:17][CH2:16][CH2:15][CH:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:13][CH2:12]1)[CH3:18])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54230472HCID 54230472, compound

Product 1

HCID 89938217HCID 89938217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a stirred solution of 3-(4-(4-fluorophenyl) piperazin-1-yl) butan-1-ol (prepared according to procedure reported in U.S. Pat. No. 5,021,420, 3.5 g, 13.87 mmol) in dichloromethane (30 ml) was added triethylamine (4.2 g, 41.61 mmol) under nitrogen atmosphere. The reaction mixture was cooled to 0-5° C. Methane sulfonyl chloride (1.58 g, 13.87 mmol) was added at 0-5° C. dropwise in 20 mins. The reaction mixture was stirred at same temp for 1 h. Progress of reaction was monitored by TLC. The reaction mixture was diluted with dichloromethane (20 ml) and washed with water (3×20 ml). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to obtain title compound (4.2 g) which was used for the next reaction without further purification.

Workup

  1. customProgress of reaction
  2. washwashed with water (3×20 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78596665701f43cda50e0f8e246114a6
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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