tert-Butylhydrazine monohydrochloride → HCID 21859122, compound

HRID 1036372Notes

Reaction equation

HRID 1036372 reaction equation
C[N:2]([CH:4]=[C:5]1[C:11](=O)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:13])C.Cl.[C:15]([NH:19]N)([CH3:18])([CH3:17])[CH3:16]>C(O)CCC.C(O)(=O)C>[C:15]([N:19]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:13])[C:5]=2[CH:4]=[N:2]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 121330652-Dimethylaminomethylene-cycloheptane-1,3-dione

Product 1

HCID 21859122HCID 21859122, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 2631-ButanolSolvent

Procedure

A solution of 1,3-cycloheptadione (2 g, mmol) was heated to reflux for 1 hour with dimethylforamide dimethylacetal (15 mL). The reaction mixture was concentrated and triturated with ether to yield 1.8 g of 2-dimethylaminomethylene-cycloheptane-1,3-dione. A solution of 2-dimethylaminomethylene-cycloheptane-1,3-dione (0.52 g, 2.9 mmol) and t-butylhydrazine hydrochloride (0.44 g, 3.5 mmol) in n-butanol (25 mL) and 0.3 mL of acetic acid was heated to reflux for 16 hours. The solvents were evaporated and the residue was chromatographed, eluting with 30% ethyl acetate/hexane to yield the title compound: 1H NMR (300 MHz, CDCl3) δ 7.85 (s, 1 H), 3.17 (m, 2 H), 2.68 (m, 2 H), 1.98 (m, 2 H), 1.89 (m, 2H) 1.68 (s, 9 H); MS (DCI/NH3) m/z 207 (M+H)+.

Workup

  1. temperatureto reflux for 16 hours
  2. customThe solvents were evaporated
  3. customthe residue was chromatographed
  4. washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6be5585fa13d410ba59d3d0cfa1ba4c1
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

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