Formaldehyde → HCID 546884, compound

HRID 261403Notes

Reaction equation

HRID 261403 reaction equation
[CH:1]12[CH2:13][CH:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=31)[CH2:5][CH2:4][NH:3][CH2:2]2.[CH2:14]=O.[OH-].[Na+]>C(O)=O>[CH3:14][N:3]1[CH2:4][CH2:5][CH:6]2[CH2:13][CH:1]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=32)[CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 12404182HCID 12404182, compound

Product 1

HCID 546884HCID 546884, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a 10 ml round bottom flask were added 1.50 g (0.00867 ) of 1,2,3,4,5,6-hexahydro-1,6-methano-3-benzazocine, 2ml of formic acid and 2 ml of 40% formaldehyde. The mixture was heated at 95-105° for 3 hours, cooled, 60 ml of 15% sodium hydroxide added, and the aqueous layer extracted with four 60-ml portions of methylene chloride. The combined extracts were concentrated in vacuo in the presence of benzene to remove water. The residue, 1.55 g (0.00829 mol), was distilled (90°-115° bath temperature, 0.1 mm) to give colorless 3-methyl-1,2,3,4,5,6-hexahydro-1,6-methano-3-benzazocine (1.1g, 68% yield). The amine was dissolved in ether and hydrogen chloride gas passed into the solution. The white precipitate obtained was filtered and recrystallized from acetone-ether: m.p. 215°-216° (d); m/e 187 (M+ -HCl).

Workup

  1. temperatureThe mixture was heated at 95-105° for 3 hours
  2. temperaturecooled
  3. extractionthe aqueous layer extracted with four 60-ml portions of methylene chloride
  4. concentrationThe combined extracts were concentrated in vacuo in the presence of benzene
  5. customto remove water
  6. distillationThe residue, 1.55 g (0.00829 mol), was distilled (90°-115° bath temperature, 0.1 mm)

Sources & evidence

ORD record
ord-5b52b345510c4075a70dd58611b25e11
Source dataset
uspto-grants-1979_08
Patent number
US04165371

Reaction notes

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