Triethylamine → 8-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-one

HRID 1686952Notes

Reaction equation

HRID 1686952 reaction equation
CC1[N:3]([C:8]2[CH:9]=[CH:10][C:11]3[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[N:13]([CH3:19])[C:12]=3[CH:20]=2)C(C)=CC=1.Cl.NO.C(N(CC)CC)C>C(O)C.O>[NH2:3][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[N:13]([CH3:19])[C:12]=2[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 672642018-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Product 1

HCID 197601958-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-oneYield 889.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

8-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (175 mgs, 0.065 mmol) was treated with hydroxylamine hydrochloride (20 eq), triethylamine (10 eq) in ethanol/water (4:1, 6 mL) and heated to 80° C. overnight. The mixture was concentrated, partitioned between EtOAc and water, dried (MgSO4) filtered and concentrated. The mixture was stirred 2 h with excess 1N HCl, neutralized to pH 7 with 1 NaOH, partitioned between EtOAc and water, dried (MgSO4) filtered and concentrated to give 8-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (110 mgs, 58%). 6.95 (d, J=7.8 Hz, 1H), 6.50-6.47 (m, 2H), 3.67 (br s, 2H), 3.30 (s, 3H), 2.61-2.57 (m, 2H), 2.32-2.28 (m, 2H), 2.11-2.08 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between EtOAc and water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompartitioned between EtOAc and water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b8de59aabc9f471089d2375549952b44
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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