3-Methoxypropylamine → HCID 101419826, compound

HRID 564298Notes

Reaction equation

HRID 564298 reaction equation
Cl[P:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N([CH2:20][CH3:21])CC)C.[CH3:22][O:23][CH2:24][CH2:25][CH2:26][NH2:27]>C1(C)C=CC=CC=1>[P:2]([N:27]([P:2]([C:21]1[CH:20]=[CH:14][CH:9]=[CH:10][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:26][CH2:25][CH2:24][O:23][CH3:22])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 16723-MethoxypropylamineHCID 8471TriethylamineHCID 66180Chlorodiphenylphosphine

Product 1

HCID 101419826HCID 101419826, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chlorodiphenylphosphine (4.9 mL, 26 mmol, 2.5 equiv.) was dissolved in dry toluene (150 mL). Under an atmosphere of argon, an excess of triethylamine (8.0 mL, 58 mmol) was syringed into the reaction flask, which was stirred for 5 minutes. 3-Methoxypropylamine (1.1 mL, 11 mmol) was then syringed dropwise under argon. A precipitate immediately formed. The reaction mixture was then allowed to stir for 36 hrs at 110° C. The ammonium salt was filtered off and the solvent and the excess triethylamine and diphenylphosphine were removed in vacuo to leave a yellowish residue. The residue was passed through a silica gel plug using a CH2Cl2/petroleum ether (1:1) mixture as the eluent. Removing the solvent and triturating with petroleum ether afforded 3.564 g of a fine white powder in 75% yield. 1H NMR (RT, 300 MHz, CDCl3): δ=1.39 (2H, br tt, JHH=8.1 Hz, JHH=6.3 Hz, CH2), 3.03 (2H, t, JHH=6.3 Hz, CH2O), 3.10 (3H, s, OCH3), 3.27-3.44 (2H, m, NCH2), 7.28-7.46 (20H, m, ArH). 31P NMR (RT, 121 MHz, CDCl3): δ=63.1 ppm (s). MS (FAB+): 458 (M+H).

Workup

  1. customA precipitate immediately formed
  2. stirringto stir for 36 hrs at 110° C
  3. filtrationThe ammonium salt was filtered off
  4. customthe solvent and the excess triethylamine and diphenylphosphine were removed in vacuo
  5. customto leave a yellowish residue
  6. customRemoving the solvent
  7. customtriturating with petroleum ether

Sources & evidence

ORD record
ord-4fe6b54d344c41f9a9ec6f458edf2f69
Source dataset
uspto-grants-2011_11
Patent number
US08067654B2

Reaction notes

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