Formaldehyde → HCID 21564487, compound

HRID 1579955Notes

Reaction equation

HRID 1579955 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:12]=3[CH2:11][CH2:10][NH:9][CH2:8][C:7]=2[C:21]=1[O:22][CH3:23].[CH2:24]=O>C(O)C.[H][H].[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:12]=3[CH2:11][CH2:10][N:9]([CH3:24])[CH2:8][C:7]=2[C:21]=1[O:22][CH3:23]

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 21564445HCID 21564445, compound

Product 1

HCID 21564487HCID 21564487, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×HCID 178418361HCID 178418361, compoundSolvent2×

Procedure

Platinum oxide (50 mg) is hydrogenated in 50 ml of ethanol by shaking in hydrogen atmosphere. To this catalyst is added a solution of 51mg of 3,4-dimethoxy-10-hydroxy-5,6,7,8,13,14-hexahydrodibenz[c,g]azecine and 1 ml of 37% formaldehyde in 5 ml of ethanol, and the mixture is shaken in hydrogen atmosphere for 6 hours. After removal of the catalyst by filtration, the mixture is evaporated to dryness under reduced pressure, and the residue (46 mg) is chromatographed on thin layer plates of silica gel containing 0.2N-sodium hydroxide [developed by chloroform - methanol (20 : 1)]. The product is recrystallized from benzene to yield 35 mg of 3,4-dimethoxy-10-hydroxy-6-methyl-5,6,7,8,13,14-hexahydrodibenz[c,g]azecine as colorless crystals having mp. 138° - 140°C. IR: νmaxNujol 3461 cm-1.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe mixture is evaporated to dryness under reduced pressure
  4. customthe residue (46 mg) is chromatographed on thin layer plates of silica gel containing 0.2N-sodium hydroxide [developed by chloroform - methanol (20 : 1)]
  5. customThe product is recrystallized from benzene

Sources & evidence

ORD record
ord-4dd95eb7d0cb471d8ed4dc9ab74d9e37
Source dataset
uspto-grants-1976_01
Patent number
US03932384

Reaction notes

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