Formaldehyde → HCID 20250790, compound

HRID 1284923Notes

Reaction equation

HRID 1284923 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[CH2:8]=O.[CH3:10][N:11]1[CH2:23][CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:14]2=[CH:15][CH:16]=[C:17]3[C:21]([NH:20][CH:19]=[CH:18]3)=[C:13]2[CH2:12]1>C(O)(=O)C>[N:1]1([CH2:8][CH:18]2[C:17]3[C:21](=[C:13]4[CH2:12][N:11]([CH3:10])[CH2:23][CH:22]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:14]4=[CH:15][CH:16]=3)[NH:20][CH2:19]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8082PiperidineHCID 13491594HCID 13491594, compound

Product 1

HCID 20250790HCID 20250790, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An ice-cooled solution of 1.51 ml (0.01524 mol) of piperidine and 1.14 ml of H2O in 4.6 ml of acetic acid is added, together with 1.14 ml (0.014 mol) of formalin, all at once, to 2.0 g (0.00762 mol) of 8-methyl-6-phenyl-6,7,8,9-tetrahydro-1H-pyrido[4,3-g]indole, with stirring and while flushing with nitrogen. The mixture is then rendered alkaline with 2N NaOH and extracted with CH2Cl2. The CH2Cl2 phase is dried over Na2SO4 and the solvent is stripped off on a rotary evaporator. The residue is chromatographed on silica gel (silica gel 60 from e. Merck, Darmstadt) using an eluent mixture of CH2Cl2 /MeOH/N(C2H5)3 (15:6:0.5). The product is dried in a desiccator over P2O5 under a water pump vacuum.

Workup

  1. customwhile flushing with nitrogen
  2. extractionextracted with CH2Cl2
  3. dry with materialThe CH2Cl2 phase is dried over Na2SO4
  4. customthe solvent is stripped off on a rotary evaporator
  5. customThe residue is chromatographed on silica gel (silica gel 60 from e. Merck, Darmstadt)
  6. additionan eluent mixture of CH2Cl2 /MeOH/N(C2H5)3 (15:6:0.5)
  7. dry with materialThe product is dried in a desiccator over P2O5 under a water pump vacuum

Sources & evidence

ORD record
ord-068a4577a20949588abf91742aba239a
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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