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

HRID 1040644Notes

Reaction equation

HRID 1040644 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-fdec67340b5b429b9af022cf860188fc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…