Sodium Bicarbonate → 7-Octyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 710490Notes

Reaction equation

HRID 710490 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=O.C([O-])(O)=O.[Na+]>CO.O>[CH2:16]([C:13]1[CH:14]=[CH:15][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH2:10][C:9]=2[CH:12]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 866618192,2,2-Trifluoro-1-(7-octyl-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)ethanone

Product 1

HCID 667267527-Octyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of Step D (0.17 g, 0.47 mmol) in a mixture of MeOH and H2O (10 ml: 1 ml), NaHCO3 (0.3 g, 3.6 mmol) was added and the reaction mixture was stirred at reflux for 2 h. The solvents were evaporated and the residue was diluted to 20 ml with EtOAc and washed with H2O, dried over MgSO4, filtered and the filtrate evaporated to dryness to give the title compound (0.12 g; 100%), as pale oil. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.93 Hz); 1.25-1.28 (m, 12H), 1.45-1.6 (m, 2H); 2.52 (tr, 2H, J=7.71 Hz); 2.85-2.93 (m, 8H); 6.85-6.92 (m, 2H); 6.97-7.0 (m, 1H).

Workup

  1. additionwas added
  2. temperatureat reflux for 2 h
  3. customThe solvents were evaporated
  4. additionthe residue was diluted to 20 ml with EtOAc
  5. washwashed with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-19ee6f9a80c64bb1a94b5d34174fa49a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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