Formaldehyde → HCID 21963842, compound

HRID 2212103Notes

Reaction equation

HRID 2212103 reaction equation
[CH3:1][CH:2]([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH2:3][C:4]#[CH:5].[C:15]1([CH:21]2[CH2:26][CH:25]3[CH2:27][CH:22]2[CH2:23][NH:24]3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:28]=O>O1CCOCC1>[CH3:1][C:2]([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:7])=[O:8])([CH3:28])[C:3]#[C:4][CH2:5][N:24]1[CH2:23][CH:22]2[CH2:27][CH:25]1[CH2:26][CH:21]2[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 21963770HCID 21963770, compoundHCID 21963808HCID 21963808, compound

Product 1

HCID 21963842HCID 21963842, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-methyl-4-(phenylsulphonyl)butyne (208 mg, 1 mmol), 5-phenyl-2-azabicyclo[2.2.1]heptane (207 mg, 1.2 mmol), and paraformaldehyde (36 mg, 1.2 mmol) in dioxane (3 ml) was degassed three times. Cuprous chloride (10 mg) was added and the mixture was heated under reflux conditions for 1 h. The mixture was cooled and evaporated in vacuo. The residue was purified by chromatography on silica using 1–7% methanol in dichloromethane. The resulting brown oil was re-purified on alumina (grade III) using 25–50% ethyl acetate in i-hexane as eluant. The resulting oil was dissolved in ethyl acetate and ethereal hydrogen chloride added dropwise to give a white crystalline solid.

Workup

  1. temperaturethe mixture was heated under reflux conditions for 1 h
  2. temperatureThe mixture was cooled
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica using 1–7% methanol in dichloromethane
  5. customThe resulting brown oil was re-purified on alumina (grade III)
  6. dissolutionThe resulting oil was dissolved in ethyl acetate
  7. additionethereal hydrogen chloride added dropwise
  8. customto give a white crystalline solid

Sources & evidence

ORD record
ord-eadd96dd9fd84ad29db8d1bfa907f479
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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