Formaldehyde → HCID 20441348, compound

HRID 1632920Notes

Reaction equation

HRID 1632920 reaction equation
[CH2:1]=O.[C:3]1([N:9]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:10]2=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Ni].C(O)C>[CH3:1][N:20]1[CH2:19][CH2:18][C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]=2[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 20441341HCID 20441341, compound

Product 1

HCID 20441348HCID 20441348, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

19.8 ml of a 35% formaldehyde solution and a spoonful of Raney Nickel are added to 20.4 g 1,2,3,4,5,6-hexahydro-6-phenylazepino[4,5-b]indole in 385 ml ethanol. The mixture is hydrogenated at room temperature. The mixture is then filtered and the filtrate concentrated to give a residue which is partitioned between ether and water. The ether phase is dried over sodium sulphate and concentrated to give the title compound as an oil which is converted into the hydrochloride, m.p. 236°-238° (from ether/ethanol).

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe mixture is then filtered
  3. concentrationthe filtrate concentrated
  4. customto give a residue which
  5. customis partitioned between ether and water
  6. dry with materialThe ether phase is dried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-61e67ba79aee46a5a4cbda0ed63c4729
Source dataset
uspto-grants-1984_10
Patent number
US04478750

Reaction notes

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