Methylamine → HCID 14476568, compound

HRID 974174Notes

Reaction equation

HRID 974174 reaction equation
[N:1]1([C@@H:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][CH2:9][CH2:8][C@H:7]2O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(Cl)(=O)=O.[CH3:23][NH2:24].[OH-].[Na+]>O1CCCC1.C(O)C.O.C(N(CC)CC)C>[CH3:23][NH:24][C@@H:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7][C@H:6]1[N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 14476566HCID 14476566, compound

Product 1

HCID 14476568HCID 14476568, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

8.2 g of the product of Step A were dissolved in 82 ml of tetrahydrofuran and 7 ml of triethylamine and after the mixture was cooled in a bath to -20° C., 3.9 ml of methane sulfonyl chloride in solution in 8 ml of tetrahydrofuran were added. After returning to ambient temperature, 35 ml of methylamine at 33% in ethanol were added and the mixture was stirred for 23 hours. The solvents were eliminated under reduced pressure and 150 ml of water and 10 ml of a solution of sodium hydroxide were added. Extraction was effected with methylene chloride and the extracts were washed with salted water, dried, filtered and concentrated to dryness under reduced pressure to obtain 8.7 g of the expected products as an orange-colored oil.

Workup

  1. customAfter returning to ambient temperature
  2. additionwere added
  3. extractionExtraction
  4. washthe extracts were washed with salted water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7810d13ed2f340939ecfaf75900bab3b
Source dataset
uspto-grants-1991_11
Patent number
US05068244

Reaction notes

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