Ammonia → HCID 14836526, compound

HRID 1614259Notes

Reaction equation

HRID 1614259 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([NH:15][CH2:16][CH2:17][CH3:18])[CH2:10]2)(=[O:3])[CH3:2].[CH:19](O)=O.C=O.N>C(Cl)Cl.O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH2:10]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 284Formic AcidHCID 712FormaldehydeHCID 14836457HCID 14836457, compound

Product 1

HCID 14836526HCID 14836526, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2.46 g (0.010 mol) of 5-acetylamino-2-n-propylamino-tetraline (Example 4.1.1) are heated with 2.34 g (0.050 mol) of formic acid and 2.2 ml of 30% formalin solution (0.022 mol of formaldehyde) for 30 minutes over a boiling water bath. The reaction mixture is shaken with 50 ml of water, 50 ml of methylene chloride and 2 ml of conc. ammonia. The aqueous phase separated off is extracted twice more with 15 ml of methylene chloride. The combined methylene chloride extract are washed with 20 ml of water, dried with sodium sulphate and concentrated by evaporation, after removal of the drying agent, in a rotary evaporator, finally at 80° C. under a total water jet vacuum. The residue is crystallised from 5 ml of acetone and 20 ml of petroleum ether. The title compound is obtained in a yield of 1.80 g (69.2% of theory) and with a melting point of 78° C.

Workup

  1. customThe aqueous phase separated off
  2. extractionis extracted twice more with 15 ml of methylene chloride
  3. extractionThe combined methylene chloride extract
  4. washare washed with 20 ml of water
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated by evaporation
  7. customafter removal of the drying agent
  8. customin a rotary evaporator
  9. customfinally at 80° C.
  10. customThe residue is crystallised from 5 ml of acetone and 20 ml of petroleum ether

Sources & evidence

ORD record
ord-27ee94a735d546bc9edf1d185aa817f8
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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