Ethylamine → HCID 46208109, compound

HRID 2041888Notes

Reaction equation

HRID 2041888 reaction equation
Cl[CH2:2][C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[F:14])([OH:6])[CH2:4]Cl.C(=O)(O)[O-].[Na+].[CH2:20]([NH2:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O1CCCC1.C(OCC)(=O)C>[Cl:13][C:9]1[C:8]([F:14])=[C:7]([C:3]2([OH:6])[CH2:4][N:22]([CH2:20][CH3:21])[CH2:2]2)[CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 6341Ethylamine2×HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 66994993HCID 66994993, compound

Product 1

HCID 46208109HCID 46208109, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1,3-dichloro-2-(3-chloro-2-fluorophenyl)propan-2-ol (0.88 g, 3.42 mmol), sodium bicarbonate (0.92 g, 10.95 mmol) and ethylamine in tetrahydrofurane (2.0 M, 1.82 ml, 3.64 mmol) in acetonitrile (15 ml) was heated at 120° C. for 30 min under microwave irradiation. Additional ethylamine in tetrahydrofurane (2.0 M, 0.91 ml, 1.82 mmol was added and the mixture was heated at 120° C. for 30 min under microwave irradiation. Aqueous sodium carbonate (50 ml, 10%) and ethyl acetate (50 ml) was added and the organic phase was collected. The aqueous phase was extracted with ethyl acetate (50 ml), the pooled organic phase was dried (MgSO4) and evaporated. The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:4 to 1:1) to give the title compound (0.28 g, 35%). The amine was converted to the fumaric acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 172-173° C. MS m/z (relative intensity, 70 eV) 229 (M+, 1), 172 (29), 157 (56), 109 (41), 58 (bp).

Workup

  1. temperaturethe mixture was heated at 120° C. for 30 min under microwave irradiation
  2. customthe organic phase was collected
  3. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  4. dry with materialthe pooled organic phase was dried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:4 to 1:1)

Sources & evidence

ORD record
ord-a417bd304b674d89922123968609aba4
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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