Hydrochloric Acid → 3-(2-Bromo-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one

HRID 1463110Notes

Reaction equation

HRID 1463110 reaction equation
[CH:1]([N-:4][CH:5](C)C)(C)[CH3:2].[Li+].C([Li])CCC.C(NC(C)C)(C)C.[Br:21][C:22]1[C:23](=O)[CH2:24][CH2:25][CH2:26][C:27]=1[O:28]C.Cl.[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>CCOCC.O>[Br:21][C:22]1[C:27](=[O:28])[CH2:26][CH2:25][CH2:24][C:23]=1[CH:33]1[CH2:32][CH2:36][CH2:2][CH2:1][N:4]([CH3:5])[C:34]1=[O:35]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 109981422-Bromo-3-methoxycyclohex-2-en-1-oneHCID 178418339Butyllithium

Product 1

HCID 131888363-(2-Bromo-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Lithium diisopropylamide was made from n-butyl lithium (1.55M in hexane, 12.9 ml) and diisopropylamine (2.8 ml) in THF (13 ml). The mixture was treated with 1-methyl-caprolactam (2.54 g) and then with 2-bromo-3-methoxycyclohexenone (4.1 g) in THF (15 ml). After 1 min. the reaction mixture was poured onto 5N HCl (8 ml) and cold water (100 ml). After 0.5 h ether was added and the organic phase separated, dried and evaporated. Recrystallisation of the residue from ethyl acetate gave the title compound (4.9 g), m.p. 112°-115° C. (d). (Found: C, 51.7; H, 6.2; N, 4.7%. C13H18BrNO2 requires: C, 52.0; H, 6.0; 4.7%).

Workup

  1. customthe organic phase separated
  2. customdried
  3. customevaporated
  4. customRecrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-cc3cfdc2d484440984616376bb3e29d0
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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