Acetic Acid → HCID 90414598, compound

HRID 876216Notes

Reaction equation

HRID 876216 reaction equation
[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(O)(=O)C.[Na].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH2:6][CH2:5]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8083Morpholine2×HCID 11430Potassium CarbonateHCID 5360545SodiumHCID 90415555HCID 90415555, compound

Product 1

HCID 90414598HCID 90414598, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-bromo-5-fluoro-tetralin-2-one (1 g, 4.11 mmol) and morpholine (0.36 mL, 4.11 mmol) in dichlormethane is added glacial acetic acid (0.52 mL, 9.05 mmol). The reaction mixture is cooled with an ice bath and sodium triacetoxyborhydride (1.74 g, 8.23 mmol) is added. The reaction mixture is stirred at r.t. overnight. Morpholine (0.2 mL) is added and stirred again at r.t. overnight. The reaction mixture is basified with potassium carbonate solution (20%) and stirred for 15 min. The organic layer is separated and the aq. layer is washed two times with dichlormethane. The organic layers are dried and concentrated. The crude product is purified by reversed phase HPLC Yield 57%, m/z 314/316 [M+H]+, rt 0.68 min, LC-MS Method X011_S03.

Workup

  1. temperatureThe reaction mixture is cooled with an ice bath
  2. stirringstirred again at r.t. overnight
  3. stirringstirred for 15 min
  4. customThe organic layer is separated
  5. washthe aq. layer is washed two times with dichlormethane
  6. customThe organic layers are dried
  7. concentrationconcentrated
  8. customThe crude product is purified by reversed phase HPLC Yield 57%, m/z 314/316 [M+H]+, rt 0.68 min, LC-MS Method X011_S03

Sources & evidence

ORD record
ord-9839a9ce385b4fdd8b72379eb0da64fb
Source dataset
uspto-grants-2015_03
Patent number
US08987249B2

Reaction notes

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