Hydrazine hydrate (1:1) → HCID 178518139, compound

HRID 485389Notes

Reaction equation

HRID 485389 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:20][C:21]([N:23]=[C:24](SC)SC)=O.O.[NH2:30][NH2:31]>O1CCCC1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:24]2[NH:31][NH:30][C:21](=[O:20])[N:23]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 12668848HCID 12668848, compound

Product 1

HCID 178518139HCID 178518139, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[3-(1-piperidinylmethyl)phenoxy]propanamine (1.76 g) in tetrahydrofuran (70 ml) was treated with dimethyl N-methoxycarbonylcarbonimidodithioate (1.27 g) at room temperature, and the mixture was stirred for 6 h. Hydrazine hydrate (2 g) was added, and the mixture was heated under reflux for 18 h. The solution was evaporated, and the residue was chromatographed to give the title compound (250 mg) as a colourless oil. tlc. System B, Rf 0.5. Nmr (D2O) 2.5,t, (1H); 2.8-3.0,m,(3H); 5.72,s,(1H); 5.8,t, (3H); 6.5,m, (2H); 6.65,t, (2H); 7.05,br.t, (2H); 7.7-8.6,m, (8H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. customThe solution was evaporated
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-a1cf75aa01734ec6b9fde1e7e6155560
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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