Triethylamine → HCID 18326812, compound

HRID 1250728Notes

Reaction equation

HRID 1250728 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(OCC)(=O)C.O1CCCC1>[CH3:24][S:25]([O:1][CH:2]1[CH2:7][CH2:6][N:5]([C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17])[CH2:4][CH2:3]1)(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 79341Piperidin-4-olHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 18326812HCID 18326812, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

10.1 g (0.1 mol) of 4-hydroxypiperidine and 11 g (0.11 mol) of triethylamine are placed in 200 ml ethyl acetate and 250 ml tetrahydrofuran and a solution of 23.3 g (0.11 mol) of 2,2,2-trichloroethyl chloroformate is added dropwise at 0-4° C. The mixture is stirred for 1 hour at 0° C. and for 1 hour at ambient temperature. The precipitate is suction filtered, the filtrate is combined at −12 to −14° C. with 12 g (0.105 mol) of methanesulphonic acid chloride and at −8 to −12° C. 12 g (0.12 mol) of triethylamine in 50 ml tetrahydrofuran are added dropwise. It is stirred for 40 minutes at −10° C., the cooling bath is removed and the mixture is stirred for 30 minutes. After washing with water and saturated saline solution it is dried with magnesium sulphate, concentrated by evaporation, the residue is triturated with diisopropylether and suction filtered. 32.4 g (91.5% of theory) of 4-methanesulphonyloxy-N-2,2,2-trichlorethoxycarbonylpiperidine are obtained as colourless crystals, melting point 93° C.

Workup

  1. filtrationfiltered
  2. stirringIt is stirred for 40 minutes at −10° C.
  3. customthe cooling bath is removed
  4. stirringthe mixture is stirred for 30 minutes
  5. washAfter washing with water and saturated saline solution it
  6. dry with materialis dried with magnesium sulphate
  7. concentrationconcentrated by evaporation
  8. customthe residue is triturated with diisopropylether and suction
  9. filtrationfiltered

Sources & evidence

ORD record
ord-68183b311cf54b9da6fd742c5c41a066
Source dataset
uspto-grants-2002_01
Patent number
US06339096B1

Reaction notes

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