Ammonia → HCID 66698092, compound

HRID 516371Notes

Reaction equation

HRID 516371 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-776db9dae97346f68cea557f7df3074d
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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