Formaldehyde → HCID 12570806, compound

HRID 443733Notes

Reaction equation

HRID 443733 reaction equation
[CH3:1][C:2]1([CH3:19])[NH:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[CH:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:20]=O>C(O)=O>[CH3:1][C:2]1([CH3:19])[CH:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[CH2:6][CH2:7][N:8]1[CH3:20]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 12570804HCID 12570804, compound

Product 1

HCID 12570806HCID 12570806, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2,3,4,5-tetrahydro-4,4-dimethyl-5-phenyl-1H-3-benzazepine (7.54 g., 0.03 mole) and 15 ml. of 36% aqueous formaldehyde in 25 ml. of 90% formic acid is refluxed for 8 hours. After the solution is concentrated to a low volume, ice and K2CO3 are added to pH 8.5 and extracted twice with 50 ml. of ethyl acetate. The combined organic extracts were washed, dried (Na2SO4) and evaporated to dryness in vacuo. Crystallization of the residue from isopropanol gives 6.0 g. (76% yield) of pure product as white crystals, m.p. 92°-93° C.

Workup

  1. concentrationAfter the solution is concentrated to a low volume, ice and K2CO3
  2. additionare added to pH 8.5
  3. extractionextracted twice with 50 ml
  4. washThe combined organic extracts were washed
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness in vacuo
  7. customCrystallization of the residue from isopropanol
  8. customgives 6.0 g

Sources & evidence

ORD record
ord-498023b906464c6faab60ef6e5c99446
Source dataset
uspto-grants-1981_04
Patent number
US04261890

Reaction notes

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