Ammonia → HCID 66698092, compound

HRID 1256530Notes

Reaction equation

HRID 1256530 reaction equation
[Cl:1][CH2:2][S:3]([N:6]([CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)(=[O:5])=[O:4].C(O)(C(F)(F)F)=O.N>C(Cl)Cl.O>[Cl:1][CH2:2][S:3]([N:6]([CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 67545518Tert-butyl 4-{[(chloromethyl)sulfonyl][3-(dimethylamino)propyl]amino}-1-piperidinecarboxylate

Product 1

HCID 66698092HCID 66698092, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the above carbamate (940 mg, 2.36 mmol) in CH2Cl2 (10 mL) was added TFA (5 mL). The reaction mixture was stirred for 1 hr. After being diluted with CH2Cl2 (10 mL) and H2O (10 mL), the mixture was made alkaline with aqueous NH3. The organic layer was separated and the aqueous layer was further extracted with CH2Cl2 (2×15 mL). The combined organic fractions were washed with H2O (2×20 mL) and dried (Na2SO4). Evaporation of the solvent gave chloro-N-[3-(dimethylamino)propyl]-N-(4-piperidinyl)methanesulfonamide (571 mg, 81%): 1H NMR (CDCl3) δ 4.46 (s, 2H), 3.76-3.68 (m, 1H), 3.35-3.31 (m, 2H), 3.16-3.14 (m, 2H), 2.70-2.63 (m, 2H), 2.28 (t, J=6.9 Hz, 2H), 2.22 (s, 6H), 1.88-1.68 (m, 7H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was further extracted with CH2Cl2 (2×15 mL)
  3. washThe combined organic fractions were washed with H2O (2×20 mL)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3ef7820b8f7f437ca8f2a3735e669e30
Source dataset
uspto-grants-2013_06
Patent number
US08461158B2

Reaction notes

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