Methanol → HCID 58227586, compound

HRID 1161214Notes

Reaction equation

HRID 1161214 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].Cl.[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.CO>>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([CH2:17][N:16]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[CH:13][C:4]=3[N+:1]([O-:3])=[O:2])[C:9]2=[O:14])[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 887MethanolHCID 2756034tert-Butyl 4-(aminomethyl)piperidine-1-carboxylate--hydrogen chloride (1/1)HCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 58227586HCID 58227586, compoundYield 88.4%

Procedure

Into a round bottom flask was combined 5-nitro-isochromen-1-one (2.0 g, 0.0094 mol), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate hydrochloride (4.7 g, 0.019 mol) and methanol (80 mL, 2 mol). The mixture was heated at reflux for 1.5 hours. The mixture was cooled to room temperature and was stirred overnight. LC-MS showed the starting material was completely consumed. Volatiles were removed and the resulting oil was purified by silical gel in a methanol:methylene chloride (0-10%) gradient. Fractions containing the desired product, as determined by TLC and LC-MS, were combined and concentrated to yield a yellow solid (3.22 g). MS m/z=388.1 (M+1).

Workup

  1. customInto a round bottom flask was combined
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 1.5 hours
  4. customwas completely consumed
  5. customVolatiles were removed
  6. customthe resulting oil was purified by silical gel in a methanol
  7. additionFractions containing the desired product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d4aa895199804b68888d6b61fb114d5b
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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