Dichloromethane → HCID 55088291, compound

HRID 628722Notes

Reaction equation

HRID 628722 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][CH2:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)Cl.[OH-].[Na+]>C(OCC)C>[CH2:7]([O:14][CH2:15][CH2:16][NH:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66679440HCID 66679440, compound

Product 1

HCID 55088291HCID 55088291, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of LAH (1.25 g, 27 mmol) in dry diethyl ether (100 mL) was added dropwise a solution of 2-benzyloxy-N-(4-fluoro-phenyl)-acetamide (33) (6.9 g, 27 mmol) in dry diethyl ether (100 mL). The addition was such as a reflux was maintained. Once the addition was completed, the reaction mixture was heated to reflux for 4 h, then poured into ice-water and DCM was added. In order to break down the aluminium salt, 2M aqueous sodium hydroxide solution was added until strong basic pH was obtained. The layers were separated and the aqueous layer was washed with DCM, dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (5-50% B, 100 g, 12 CV, 60 mL/min) to afford 5.5 g (84%) of (2-benzyloxy-ethyl)-(4-fluoro-phenyl)-amine (34) as a yellow oil. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 44.0, 68.3, 72.8, 113.7 (d, JCF=7 Hz), 115.3 (d, JCF=22 Hz), 127.5, 127.6 (d, JCF=3 Hz), 128.3, 137.8, 144.5, 154.1, and 157.2.

Workup

  1. additionThe addition
  2. temperaturewas maintained
  3. additionOnce the addition
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for 4 h
  6. additionwas added
  7. additionwas added until strong basic pH
  8. customwas obtained
  9. customThe layers were separated
  10. washthe aqueous layer was washed with DCM
  11. customdried
  12. concentrationconcentrated in vacuo
  13. customThe crude material was purified by silica gel chromatography
  14. washeluting with petrol (A) and ethyl acetate (B) (5-50% B, 100 g, 12 CV, 60 mL/min)

Sources & evidence

ORD record
ord-03107daaef8641c29f46fe02750b1962
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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