Triethylamine → HCID 178505324, compound

HRID 617240Notes

Reaction equation

HRID 617240 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]3)=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:17][C@H:18]3[CH2:19][CH2:20][C@H:21]([O:24][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][CH2:23]3)=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178521589HCID 178521589, compound

Product 1

HCID 178505324HCID 178505324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

447 ml of methanesulphonyl chloride were added portionwise within 20 minutes while cooling with an ice bath to a mixture of 1157 g of trans-N-(7-chloro-quinolin-4-yl)-4-aminocyclohexanol and 868 ml of triethylamine in 6.1 l of dichloromethane. After a clear solution formed transiently the product began to separate. After 2 hours the mixture was filtered and the filtrate was evaporated to dryness. Filter residue and evaporation residue were combined and triturated. in 8 l of water. The mixture was again filtered, washed with a further 8 l of water and thereafter with 4 l of isopropanol and the product obtained was dried at 50° C./12 mbar. Yield: 2028 g (90%) of trans-N-(7-chloro-quinolin-4-yl)-4-methanesulphonyloxy-cyclohexylamine, m.p.: 154-159° C.

Workup

  1. customAfter a clear solution formed transiently the product
  2. customto separate
  3. filtrationAfter 2 hours the mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. customFilter residue and evaporation residue
  6. customtriturated
  7. filtrationThe mixture was again filtered
  8. washwashed with a further 8 l of water
  9. customwith 4 l of isopropanol and the product obtained
  10. customwas dried at 50° C./12 mbar

Sources & evidence

ORD record
ord-56cdc962bd60416086cb4f49339596ae
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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