Hydrochloric Acid → HCID 86690341、化合物

HRID 520279ノート

反応式

HRID 520279 の反応式
[Cl:1][CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5]1.[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>C(O)(C)C.C1(C)C=CC=CC=1.C(O)C>[ClH:1].[F:30][C:16]([F:15])([F:29])[C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][N:4]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]=[CH:5]3)[CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 45187433-(2-Chloroethyl)quinazolin-4(3H)-one

生成物 1

HCID 86690341HCID 86690341、化合物収率 69%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 3776Isopropanol溶媒

実験手順

The following were added to a 250 mL reactor: 3-(2-chloroethyl) quinazoline-4 (3H)-one (1 g, 4.79 mmol), 1-(3-(trifluoromethyl)phenyl)piperazine (1,103 g, 4.79 mmol), sodium carbonate (0.762 g, 7.19 mmol), sodium iodide (0.072 g, 0.479 mmol), ethanol (50 ml) and toluene (150 ml). The reaction medium was kept under agitation and reflux for a period of twenty hours, during which 150 ml of the solvent were removed slowly with the assistance of a Dean-Stark. To the resulting mixture, 100 mL of an aqueous solution of acetic acid were added at 10% and 150 mL of ethyl acetate. The mixture was agitated, the organic phase separated, washed with 2 portions of 50 mL of a 5% sodium bicarbonate solution, dry with MgSO4, filtered and evaporated to dryness, yielding the raw product as a slightly yellowish oil. This oil was dissolved in isopropanol, adding 2 mL of concentrated HCl under agitation to the resulting solution. This agitation was maintained for two hours in order to complete the precipitation of the hydrochloride. The resulting solid was filtered and vacuum dried, yielding 1.45 g of 3-(2-(4-(3-(trifluoromethyl)phenyl)piperazine-1-yl)ethyl)quinazoline-4 (3H)-one hydrochloride (3.3 mmol, yield=69%).

後処理

  1. additionThe following were added to a 250 mL reactor
  2. customwere removed slowly with the assistance of a Dean-Stark
  3. additionTo the resulting mixture, 100 mL of an aqueous solution of acetic acid were added at 10% and 150 mL of ethyl acetate
  4. customthe organic phase separated
  5. washwashed with 2 portions of 50 mL of a 5% sodium bicarbonate solution
  6. dry with materialdry with MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customyielding the raw product as a slightly yellowish oil
  10. temperatureThis agitation was maintained for two hours in order
  11. customthe precipitation of the hydrochloride
  12. filtrationThe resulting solid was filtered
  13. customvacuum dried

出典と根拠

ORDレコード
ord-189b2f97cecc4c6ca9715ea316809a7f
出典データセット
uspto-grants-2016_05
特許番号
US09326984B2

反応ノート

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