Diisopropylethylamine → HCID 18519986, compound

HRID 1936730Notes

Reaction equation

HRID 1936730 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[CH3:11][O:12][NH2:13].[C:14]1(=[O:21])[CH:20]=[CH:19][CH2:18][CH2:17][CH:16]=[CH:15]1>C(O)(C)C>[CH3:11][O:12][N:13]1[CH:19]2[CH2:18][CH2:17][CH:16]1[CH2:15][C:14](=[O:21])[CH2:20]2

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 109204632,6-Cycloheptadien-1-one

Product 1

HCID 18519986HCID 18519986, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

N,N-Diisoproylethylamine (14.5 ml) was added dropwise to a stirred suspension of O-methylhydroxylamine hydrochloride (2.32 g) in isopropyl alcohol (25 ml). After 30 minutes cyclohepta-2,6-dienone (3.0 g) in isopropyl alcohol (5 ml) was added dropwise. After 24 hours N,N-diisopropylethylamine (4.9 ml) was added. After 6 hours the mixture was allowed to stand at room temperature overnight. The mixture was evaporated under reduced pressure, diethyl ether added and the resulting mixture extracted with 2M hydrochloric acid (x3). The combined aqueous fractions were washed with diethyl ether (x3), neutralised with sodium hydroxide and extracted with diethyl ether (x3). The combined extracts were washed with brine, dried (MgSO4) and evaporated under reduced pressure. Kugelrohr distillation gave 8-methoxy-8-azabicyclo[3.2.1]octan-3-one (0.86 g).

Workup

  1. waitto stand at room temperature overnight
  2. customThe mixture was evaporated under reduced pressure, diethyl ether
  3. additionadded
  4. extractionthe resulting mixture extracted with 2M hydrochloric acid (x3)
  5. washThe combined aqueous fractions were washed with diethyl ether (x3)
  6. extractionextracted with diethyl ether (x3)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure
  10. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-4c8e9ae7457343029b6921c0978c78ca
Source dataset
uspto-grants-2002_05
Patent number
US06391883B1

Reaction notes

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