Hydrochloric Acid → [1-(Pyridin-4-yl)piperidin-4-yl]methanamine

HRID 49835

反応式

HRID 49835 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13]O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C1(=O)[NH:19]C(=O)C2=CC=CC=C12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.Cl.O.NN>C1COCC1.CCO.C(Cl)Cl.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH2:19])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 24654Hydrazine hydrate (1:1)HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanol

生成物 1

HCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine収率 56.7%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

A solution of 1-(4-pyridyl)piperidine-4-methanol (5.87 g, 30.6 mmol), phthalimide (4.59 g, 31.2 mmol), and triphenylphosphine (8.10 g, 30.9 mmol) in 125 mL of THF at −5° C. was treated with a solution of diethyl azodicarboxylate (5.38 g, 30.9 mmol) in THF (40 mL). After 16 h, the mixture was poured into EtOAc and 1 N HCl. The aqueous layer was washed with EtOAc (2×), pH adjusted to 12 by addition of 5 N NaOH, and washed with EtOAc (3×). The combined organic extracts were dried (K2CO3) and concentrated, yielding 8.45 g (86%). The crude material (5.47 g, 17.0 mmol) was then treated with hydrazine hydrate (3.5 mL, 60.0 mmol) in EtOH (50 ML). The mixture was heated at 75° C. for 5 h, cooled, diluted with CH2Cl2 (100 mL), and cooled to 0° C. The solid was removed by filtration; and the filtrate was concentrated, yielding 3.32 g of the title compound which was used without further purification.

後処理

  1. washThe aqueous layer was washed with EtOAc (2×)
  2. additionpH adjusted to 12 by addition of 5 N NaOH
  3. washwashed with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried (K2CO3)
  5. concentrationconcentrated
  6. customyielding 8.45 g (86%)
  7. temperaturecooled
  8. temperaturecooled to 0° C
  9. customThe solid was removed by filtration
  10. concentrationand the filtrate was concentrated

出典と根拠

ORDレコード
ord-dad19736bdea4fb78ee7e9065f930181
出典データセット
uspto-grants-2004_03
特許番号
US06710057B2

関連ノート

読み込み中…