Triethylamine → HCID 18357139, compound

HRID 427434Notes

Reaction equation

HRID 427434 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].NC[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[CH2:26]([N:28](CC)CC)C>ClCCl>[N:23]1[CH:24]=[CH:25][C:20]([N:17]2[CH2:16][CH2:15][N:14]([C:11]3[CH:10]=[CH:9][CH:8]=[CH:13][C:12]=3[CH2:26][NH:28][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:19][CH2:18]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18357039HCID 18357039, compound

Product 1

HCID 18357139HCID 18357139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonyl chloride (0.155 ml) in dichloromethane (10 ml) was added dropwise to a stirred solution of 1-(4-aminomethylphenyl)-4-(4-pyridyl)piperazine (536 mg) in dichloromethane (50 ml) containing triethylamine (0.5 ml). The resulting solution was stirred at ambient temperature for 7 hours. The solution was evaporated and the residue was extracted with ethyl acetate. The ethyl acetate extracts were washed with water, sodium bicarbonate solution, brine, dried (MgSO4) and evaporated. The solid residue was recrystallised from methanol to give 1-(4-pyridyl)-4-(methanesulphonamidomethylphenyl)piperazine (356 mg) as a solid, m.p.236-238° C.; microanalysis found: C,59.3; H,6.4; N,16.2%; C17H22N4O2S requires: C,58.8; H,6.4; N,16.2%; NMR: 2.8(s,3H), 3.15-3.3(m,4H), 3.4-3.55(m,4H), 4.00-4.10(d,2H,), 6.80-6.90(d,2H), 6.90-7.00(d,2H), 7.15-7.25(d,2H), 7.3—7.5(t,1H), 8.20(d,1H); MS: m/z 311 (MH)+.

Workup

  1. customThe solution was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe ethyl acetate extracts were washed with water, sodium bicarbonate solution, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe solid residue was recrystallised from methanol

Sources & evidence

ORD record
ord-b1657b9b22b249d79fa90a2e49b03ac5
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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