Triethylamine → HCID 11705658, compound

HRID 1091979Notes

Reaction equation

HRID 1091979 reaction equation
[CH2:1]([C@@:3]1([CH2:10][S:11](Cl)(=[O:13])=[O:12])[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4]1)[CH3:2].Cl.[F:16][C:17]([F:34])([F:33])[CH2:18][O:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([C@:3]1([CH2:10][S:11]([N:28]2[CH2:29][CH2:30][CH:25]([O:24][C:23]3[CH:22]=[CH:21][C:20]([O:19][CH2:18][C:17]([F:16])([F:33])[F:34])=[CH:32][CH:31]=3)[CH2:26][CH2:27]2)(=[O:13])=[O:12])[NH:4][C:5](=[O:9])[NH:6][C:7]1=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 55280267HCID 55280267, compoundHCID 66593025HCID 66593025, compound

Product 1

HCID 11705658HCID 11705658, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(4S)-4-ethyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (WO 2004/024698) (869 mg) was added to a stirred solution of 4-[4-(2,2,2-trifluoroethoxy)phenoxy]piperidine hydrochloride (750 mg) and triethylamine (1.68 ml) in dichloromethane (50 ml) and the reaction stirred at ambient temperature for 2 hours. The solvents were removed in vacuo and the residue stirred in water for 2 hours. The resulting solid was filtered off, washed with water then ether and dried to give the title compound (1.13 g); NMR Spectrum: (DMSOd6) 0.78 (t, 3H), 1.25 (m, 2H), 1.66 (m, 4H), 1.94 (m, 2H), 3.11 (m, 2H), 3.49 (d, 1H), 3.58 (m, 1H), 4.41 (m, 1H), 4.64 (q, 2H), 6.97 (m, 4H), 8.5 (s, 1H), 10.71 (s, 1H); Mass Spectrum: M−H− 478.

Workup

  1. customThe solvents were removed in vacuo
  2. stirringthe residue stirred in water for 2 hours
  3. filtrationThe resulting solid was filtered off
  4. washwashed with water
  5. dry with materialether and dried

Sources & evidence

ORD record
ord-02d8187556a9480eabd656d901df9df8
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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