Triethylamine → HCID 178481023, compound

HRID 2384541Notes

Reaction equation

HRID 2384541 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[C:15](=[O:20])[CH2:14]2)[CH2:9][CH2:8]1.C(N(CC)CC)C>C1COCC1>[CH3:4][S:1]([O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[C:15](=[O:20])[CH2:14]2)[CH2:11][CH2:12]1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178481021HCID 178481021, compound

Product 1

HCID 178481023HCID 178481023, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

109 g of mesyl chloride in 250 ml THF are added dropwise to 150 g (trans)-1-hydroxy-4-(4-methyl-3-oxo-piperazin-1-yl)-cyclohexane and 162 ml triethylamine in 2300 ml THF in such a way that the temperature does not exceed 35° C. After 25 min the suspension is filtered and washed with 300 ml THF. The filtrate is evaporated down in vacuo at 40° C. to a total mass of 520 g. 230 ml ethyl acetate are added to the suspension. After 15 min the mixture is filtered and the precipitate is washed with 230 ml of ethyl acetate and 150 ml of methyl-tert-butyl ether. After drying, 153.1 g product are obtained.

Workup

  1. customdoes not exceed 35° C
  2. filtrationAfter 25 min the suspension is filtered
  3. washwashed with 300 ml THF
  4. customThe filtrate is evaporated down in vacuo at 40° C. to a total mass of 520 g
  5. addition230 ml ethyl acetate are added to the suspension
  6. filtrationAfter 15 min the mixture is filtered
  7. washthe precipitate is washed with 230 ml of ethyl acetate and 150 ml of methyl-tert-butyl ether
  8. customAfter drying

Sources & evidence

ORD record
ord-5cf1c7921401485bbf351b3af9491268
Source dataset
uspto-grants-2012_09
Patent number
US08263768B2

Reaction notes

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