1-Iodopropane → HCID 22345165, compound

HRID 2232923Notes

Reaction equation

HRID 2232923 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=2)=[CH:3][CH:2]=1.I[CH2:19][CH2:20][CH3:21]>>[CH2:19]([N:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14]([F:15])([F:16])[F:17])[CH:8]=2)[CH2:3][CH2:2]1)[CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 336431-IodopropaneHCID 22345214HCID 22345214, compound

Product 1

HCID 22345165HCID 22345165, compound

Conditions

Temperature
100 °C

Procedure

4-Pyridin-4-yl-2-trifluoromethyl-phenylamine (270 mg) was dissolved in 1-iodo-propane (2 ml) and heated to 100° C. for 2 h. Then the voilatiles were evaporated and the residue redissolved in abs EtOH (20 ml) and NaBH4 (800 mg) was added portions wise at −20° C. The mixture was then allowed to reach r.t. and stirred over night. To the mixture was added 10% Na2CO3 solution (20 ml). The aqueous layer was extracted with CH2Cl2 and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v)). Collection of the fractions containing pure product and evaporation of the solvent afforded pure 4-(1-Propyl-1,2,3,6-tetrahydro-pyridine-4-yl)-2-trifluoromethyl-phenylamine (200 mg). MS m/z (rel. intensity, 70 eV)) 284 (M+, 53), 255 (bp), 144 (40), 127 (39), 70 (39). Rf 0.28 (MeOH)

Workup

  1. customThen the voilatiles were evaporated
  2. dissolutionthe residue redissolved in abs EtOH (20 ml)
  3. additionNaBH4 (800 mg) was added portions wise at −20° C
  4. customto reach r.t.
  5. additionTo the mixture was added 10% Na2CO3 solution (20 ml)
  6. extractionThe aqueous layer was extracted with CH2Cl2
  7. dry with materialthe combined organic phases were dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v))
  11. customCollection of the fractions
  12. additioncontaining pure
  13. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-d6acb3e4a00d4f9db4da4eab06fa2a29
Source dataset
uspto-grants-2010_05
Patent number
USRE041315E1

Reaction notes

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