Hydrochloric Acid → 2-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile

HRID 896254ノート

反応式

HRID 896254 の反応式
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>C1COCC1.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[NH2:1][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 223496205-Methoxy-4-[(1-methylpiperidin-4-yl)methoxy]-2-nitrobenzonitrile

生成物 1

HCID 223496642-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile収率 75.5%

試薬・触媒・溶媒 3

HCID 5963Benzyltrimethylammonium chloride触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

2-nitro-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile (1.1 g, 3.6 mmol) in THF (20 ml) in presence of benzyltrimethylammonium chloride (334 mg, 1.8 mmol) was treated by a slow addition of Na2S2O4 (3.1 g, 18 mmol) in water (20 ml). After 0.5 h, HCl (6N, 20 ml) was added to the mixture, which was stirred at 60° C. for 5 h. The mixture was cooled to room temperature, extracted with ethylacetate. The aqueous phase was made basic with Na2 CO3 (solid), and extracted with ethylacetate. The organic phase was dried over MgSO4, concentrated, to give a yellow solid (748 mg, 75%) of title compound.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-274159f323c348ee8e4688369550225b
出典データセット
uspto-grants-2005_07
特許番号
US06919338B2

反応ノート

読み込み中…