Isopropylamine → HCID 16494785, compound

HRID 349516Notes

Reaction equation

HRID 349516 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH:9]([NH2:12])([CH3:11])[CH3:10]>C1COCC1.C(O)C>[N:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:12][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 6427994-(Bromomethyl)pyridine

Product 1

HCID 16494785HCID 16494785, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

4-Bromomethylpyridine (1 g) was suspended in THF:ethanol (5:1) and cooled to 0–5° C. Isopropylamine (1.01 ml) was added and the resultant mixture allowed to reach room temperature. After 24 h, the mixture was concentrated under reduced pressure and the residue purified using SPE (silica, eluting with DCM:methanol 1:1, 3:7, 1:4 and methanol) to give an impure sample of the title compound. Further purification using SPE (silica, eluting with DCM, ethyl acetate, acetonitrile, methanol) gave the title compound (0.25 g) as a white solid.

Workup

  1. temperaturecooled to 0–5° C
  2. customto reach room temperature
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue purified
  5. washSPE (silica, eluting with DCM:methanol 1:1, 3:7, 1:4 and methanol)

Sources & evidence

ORD record
ord-cd974ce190aa462597d93e60baf256d1
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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