Dichloromethane → HCID 178484833, compound

HRID 722033Notes

Reaction equation

HRID 722033 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(Cl)Cl.[C:9]([O:13][C:14]([NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:23][CH3:24])[CH2:19][CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])O.[Na+]>O.C(N(CC)CC)C>[C:9]([O:13][C:14]([NH:16][C@H:17]1[CH2:18][CH2:19][C@H:20]([N:23]([CH3:24])[S:2]([CH3:1])(=[O:4])=[O:3])[CH2:21][CH2:22]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178484832HCID 178484832, compound

Product 1

HCID 178484833HCID 178484833, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

254 μl of methanesulfonyl chloride was added to a methylene chloride solution containing 500 mg of N-tert-butoxycarbonyl-N′-methyl-trans-1,4-cyclohexanediamine (Reference Example 10-14 (1)) and 763 μl of triethylamine, and the mixture was stirred at room temperature for 14 hours. To the reaction mixture were added water, followed by an aqueous saturated sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was-washed with an aqueous saturated sodium hydrogencarbonate, water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was suspended in diisopropyl ether, and collected by filtration to obtain N-tert-butoxycarbonyl-N′-methyl-N′-methylsulfonyl-trans-1,4-cyclohexanediamine. Subsequently, this compound was treaded with hydrochloric acid to obtain N-methyl-N-methylsulfonyl-trans-1,4-cyclohexanediamine (Reference Example 10-18 in Table 11).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was-washed with an aqueous saturated sodium hydrogencarbonate, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9d46e78f4704426ab2cba64374afa01d
Source dataset
uspto-grants-2006_11
Patent number
US07138397B2

Reaction notes

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