Hydrochloric Acid → 1-(9-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)-4-phenethylpiperazin-2-one hydrochloride

HRID 2365388ノート

反応式

HRID 2365388 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]3=[O:25])[CH:9]=2)[C:4]2[CH2:26][CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][C:3]1=2.[ClH:37]>CO.CCOCC>[ClH:37].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]3=[O:25])[CH:9]=2)[C:4]2[CH2:26][CH2:27][NH:28][CH2:29][C:3]1=2

参加物

5

反応物 2

HCID 313Hydrochloric Acid2 回HCID 67986813tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

生成物 1

HCID 679695921-(9-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)-4-phenethylpiperazin-2-one hydrochloride収率 33%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (35 mg, 0.071 mmol) was dissolved in MeOH (2 mL), and 2 N HCl in Et2O (10 mL) was added. The reaction was allowed to proceed for 18 h. The mixture was concentrated, and the residue was partitioned between CH2Cl2 and sat. Na2CO3 solution. The organic phase was removed, and the aqueous phase was back extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness. The residue was dissolved in MeOH (1 mL), treated with 2 N HCl in Et2O (12 μL, 0.024 mmol), and concentrated to provide the title compound (10 mg, 33%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.60 (d, J=8.3 Hz, 1H), 7.45 (s, 1H), 7.41-7.34 (m, 4H), 7.33-7.27 (m, 1H), 7.67 (d, J=8.2 Hz, 1H), 4.54 (s, 2H), 4.24-4.15 (m, 2H), 4.15-4.03 (m, 2H), 3.91-3.76 (m, 2H), 3.72 (s, 3H), 3.61-3.54 (m, 4H), 3.22-3.16 (m, 2H), 3.14-3.08 (m, 2H); ESI MS m/z 389 [M+H]+; HPLC (Method B) 94.4% (AUC), tR=10.2 min.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and sat. Na2CO3 solution
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was back extracted with CH2Cl2
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. dissolutionThe residue was dissolved in MeOH (1 mL)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-4aa9eb9cd51d41a28a8c883544d5391c
出典データセット
uspto-grants-2014_04
特許番号
US08697700B2

反応ノート

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