Cyclopropylamine → HCID 59295941, compound

HRID 2233392Notes

Reaction equation

HRID 2233392 reaction equation
[Cl:1][C:2]1[C:3]([S:23](Cl)(=[O:25])=[O:24])=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:5][CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1>>[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][CH:19]=[C:4]([O:5][CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[C:3]=1[S:23]([NH:30][CH:27]1[CH2:29][CH2:28]1)(=[O:24])=[O:25]

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 59295944HCID 59295944, compound

Product 1

HCID 59295941HCID 59295941, compound

Procedure

tert-Butyl 4-[3,4-dichloro-2-(chlorosulfonyl)phenoxy]piperidine-1-carboxylate (0.70 g, 1.8 mmol) was dissolved in cyclopropylamine (8 ml) and stirred at room temperature for 30 min. The solution was concentrated in in vacuo and then azeotroped with toluene (4 times). The residue was redissolved in dichloromethane: trifluoroacetic acid/1:1 (20 ml) and stirred at room temperature for 15 min. The solution was concentrated in vacuo, then partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The aqueous was reextracted with ethyl acetate (4 times), and the combined organics dried over anhydrous potassium carbonate. Concentration in vacuo afforded the title compound as a white powder (0.70 g).

Workup

  1. concentrationThe solution was concentrated in in vacuo
  2. customazeotroped with toluene (4 times)
  3. dissolutionThe residue was redissolved in dichloromethane
  4. stirringtrifluoroacetic acid/1:1 (20 ml) and stirred at room temperature for 15 min
  5. concentrationThe solution was concentrated in vacuo
  6. custompartitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialthe combined organics dried over anhydrous potassium carbonate
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-286f30ab196d4a57acac17cec18bae00
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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