Methanol → N-(1'-(2-(2-Aminoethoxy)ethyl)-4-oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfon-amide dihydrochloride

HRID 1093903Notes

Reaction equation

HRID 1093903 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:31](=[CH:32][CH:33]=1)[O:30][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:34])(=[O:4])=[O:3].CO.[Cl:37]CCl>Cl.C(O)(=O)C>[ClH:37].[ClH:37].[NH2:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][N:14]1[CH2:13][CH2:12][C:11]2([CH2:10][C:9](=[O:34])[C:8]3[C:31](=[CH:32][CH:33]=[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:7]=3)[O:30]2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 57903876tert-Butyl 2-(2-(6-(methylsulfonamido)-4-oxospiro[chroman-2,4'-piperidine]-1'-yl)ethoxy)ethylcarbamate2×

Product 1

HCID 66636871N-(1'-(2-(2-Aminoethoxy)ethyl)-4-oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfon-amide dihydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

Ten drops of concentrated hydrochloric acid was added to a solution of tert-butyl 2-(2-(6-(methylsulfonamido)-4-oxospiro[chroman-2,4′-piperidine]-1′-yl)ethoxy)ethylcarbamate (12, 0.51 g, 1.02 mmol) in 5 mL of glacial acetic acid and the resulting solution was stirred at room temperature. After ˜1.5 hours, TLC (silica gel, 10% methanol in dichloromethane, UV visualization) shows complete disappearance of starting compound 12 (Rf=0.2−0.3) and a new spot at the origin. Volatile components were removed under reduced pressure on the rotary evaporator. Toluene (˜10 mL) was added and evaporated under reduced pressure on the rotary evaporator. The toluene addition and evaporation was repeated two more times and the residue was dried under high vacuum. The resulting residue was triturated with 3 mL of diethyl ether, resulting in formation of a tan solid. The diethyl ether was removed under reduced pressure on the rotary evaporator followed by high vacuum to give a tan solid.

Workup

  1. customVolatile components were removed under reduced pressure on the rotary evaporator
  2. additionToluene (˜10 mL) was added
  3. customevaporated under reduced pressure on the rotary evaporator
  4. additionThe toluene addition and evaporation
  5. customthe residue was dried under high vacuum
  6. customThe resulting residue was triturated with 3 mL of diethyl ether
  7. customresulting in formation of a tan solid
  8. customThe diethyl ether was removed under reduced pressure on the rotary evaporator
  9. customto give a tan solid

Sources & evidence

ORD record
ord-9b2f93e5fb1f4fc8a9d0e27951571969
Source dataset
uspto-grants-2012_03
Patent number
US08133695B2

Reaction notes

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