Triethylamine hydrochloride → 2,4-Dichloro-6-piperidinoquinazoline

HRID 855643Notes

Reaction equation

HRID 855643 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=O)[NH:11][C:10]3=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:19].C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:29]>>[Cl:19][C:12]1[N:11]=[C:10]([Cl:29])[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=2)[N:13]=1

Participants

4

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 24813Phosphorus oxychlorideHCID 134217986-Piperidin-1-yl-1H-quinazoline-2,4-dione

Product 1

HCID 134217992,4-Dichloro-6-piperidinoquinazolineYield 91%

Procedure

To 6-Piperidin-1-yl-1H-quinazoline-2,4-dione (522 mg, 2.13 mmol) and triethyl amine hydrochloride (1.2 g, 8.5 mmol) was added POCl3 (20 mL) and the solution was heated to 120 C for 72 h. POCl3 was removed in vacuum and the resulting brown oil was quenched with ice water and treated with saturated NaHCO3, to afford a tan solid. Filtration and drying in vacuum gave title compound 550 mg (91% yield). HPLC tr=8.56 min (100%), FIA m/z 282.1 (M+H), HNMR (500 MHz, dmso): δ 8.05–8.00 (1H, d), 7.85–7.80 (1H, d), 7.20 (1H s), 5.50–4.40 (4H, m), 1.70–1.60 (6H, m).

Workup

  1. temperaturethe solution was heated to 120 C for 72 h
  2. customPOCl3 was removed in vacuum
  3. customthe resulting brown oil was quenched with ice water
  4. additiontreated with saturated NaHCO3
  5. customto afford a tan solid
  6. filtrationFiltration
  7. customdrying in vacuum

Sources & evidence

ORD record
ord-65b9e88e8d8e4ca0b0109aeba91089c9
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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