Propylamine → HCID 86652729, compound

HRID 1895919Notes

Reaction equation

HRID 1895919 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1C=CN=C1)=[O:2].[F:13][C:14]([F:33])([F:32])[C:15]1[CH:16]=[C:17]([S:21]([N:24]2[CH2:29][CH2:28][CH:27]([O:30]N)[CH2:26][CH2:25]2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.[CH2:34](N(CC)CC)C.C(N)CC>C(Cl)Cl>[CH2:12]([NH:8][C:1]([NH:3][O:30][CH:27]1[CH2:28][CH2:29][N:24]([S:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:33])([F:32])[F:13])[CH:16]=2)(=[O:23])=[O:22])[CH2:25][CH2:26]1)=[O:2])[CH2:11][CH3:34]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67118429O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

Product 1

HCID 86652729HCID 86652729, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (194 mg, 1.20 mmol) was added to a solution of O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (195 mg, 0.60 mmol) and triethylamine (121 mg, 1.20 mmol) in CH2Cl2 (5 ml) and stirred at room temperature for 17 hours. Propan-1-amine (35.0 mg, 0.60 mmol) was added to the reaction mixture and stirred at room temperature for another 17 hours. The resulting precipitaion was collected, washed with aqueous 1 N HCl solution (10 ml×3), aqueous NaHCO3 solution (10 ml×3), diethyl ether (10 ml×2) to give 1-propyl-3-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)urea (215 mg, 88%) as a white solid: LCMS: 410 [M+1]+. 1H NMR (DMSO-d6) δ: 0.77 (t, 3H), 1.37 (m, 2H), 1.73 (m, 2H), 1.88 (m, 2H), 2.87 (m, 4H), 3.17 (m, 2H), 3.61 (t, 1H), 6.63 (t, 1H), 7.90 (m, 2H), 8.08 (m, 2H), 8.79 (s, 1H).

Workup

  1. stirringstirred at room temperature for another 17 hours
  2. customThe resulting precipitaion was collected
  3. washwashed with aqueous 1 N HCl solution (10 ml×3), aqueous NaHCO3 solution (10 ml×3), diethyl ether (10 ml×2)

Sources & evidence

ORD record
ord-11d78e73e5e44c80a639c94d95aa3fe5
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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