Formamide → HCID 178419910, compound

HRID 1908035Notes

Reaction equation

HRID 1908035 reaction equation
[NH2:1][CH:2]1[C:11]2([CH2:16][CH2:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13][CH2:12]2)[O:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[CH:28]([NH2:30])=O.[OH-].[Na+].[H][H]>[Pd]>[NH:14]1[CH2:13][CH2:12][C:11]2([C:2]3[N:1]=[CH:28][NH:30][C:3]=3[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[O:10]2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 713FormamideHCID 14798Sodium HydroxideHCID 58551336HCID 58551336, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178419910HCID 178419910, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
180 °C

Procedure

Benzyl 3-amino-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylate (600 mg, 1.64 mmol) was added portion-wise to formamide (3.0 mL, 75 mmol) and the mixture was heated at 180° C. for 2 h. After cooling to room temperature, 3 mL of 1N NaOH was added and the resulting solution was extracted with dichloromethane. The organics were combined and washed with brine, dried over sodium sulfate, and evaporated to dryness. The crude material was filtered through silica gel eluting with 0-10% methanol in dichloromethane. The combined fractions were evaporated, and the residue (400 mg) was dissolved in methanol (5 mL). Pd/C (210 mg, 0.20 mmol) was added and the mixture was stirred under a balloon of hydrogen. The reaction was filtered and the filtrate evaporated to give 1H-spiro[chromeno[4,3-d]imidazole-4,4′-piperidine]. ESI-MS m/z calc. 241.3. found 242.5 (M+1)+; Retention time: 0.27 minutes (3 min run).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting solution was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. filtrationThe crude material was filtered through silica gel eluting with 0-10% methanol in dichloromethane
  7. customThe combined fractions were evaporated
  8. dissolutionthe residue (400 mg) was dissolved in methanol (5 mL)
  9. filtrationThe reaction was filtered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-791eafad96b843f2a0880076ab4603ee
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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