Diisopropylethylamine → HCID 18519986, compound

HRID 1368182Notes

Reaction equation

HRID 1368182 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-Diisopropylethylamine (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 (×3). The combined aqueous fractions were washed with diethyl ether (×3), neutralised with sodium hydroxide and extracted with diethyl ether (×3). 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 (×3)
  5. washThe combined aqueous fractions were washed with diethyl ether (×3)
  6. extractionextracted with diethyl ether (×3)
  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-fc7031d1a15b4f6bb4e8d904d32409aa
Source dataset
uspto-grants-2003_06
Patent number
US06573275B1

Reaction notes

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