1,1-Dimethylethyl 4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinecarboxylate → 1-(2-Fluoroethyl)-4-(4-piperidinyl)piperazine

HRID 419423ノート

反応式

HRID 419423 の反応式
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1>CO.Cl>[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:6][CH2:5]1

参加物

4

反応物 1

HCID 594526881,1-Dimethylethyl 4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinecarboxylate

生成物 1

HCID 594527951-(2-Fluoroethyl)-4-(4-piperidinyl)piperazine

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

1,1-Dimethylethyl 4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinecarboxylate (10.2 g, 32.3 mmol) was dissolved in 40 mL of MeOH and 40 mL of 37% HCl. Reaction was stirred for 1 h, concentrated in vacuo and then a small amount of H2O was added back to solubilize the HCl salt of the product. When everything was in solution, solid K2CO3 was added to neutralize. The mixture was then concentrated in vacuo to remove H2O. Residue taken up in DCM and solids were filtered and washed with 20% MeOH/DCM. Filtrate was concentrated in vacuo and residue taken up in diethyl ether. Solids filtered and washed with diethyl ether several times. Combined filtrates were concentrated in vacuo to give desired product in two crops (2.42 g and 1.85 g) without further purification. Batches were combined together to give the title compound of step D (4.3 g, 68%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.40-4.58 (m, 2H), 3.15 (s, 1H), 2.91 (d, J=12.1 Hz, 2H), 2.35-2.59 (m, 12H), 2.15 (tt, J=11.36, 3.67 Hz, 1H), 1.63 (d, J=12.10 Hz, 2H), 1.19 (qd, J=11.85, 4.03 Hz, 2H).

後処理

  1. customReaction
  2. concentrationconcentrated in vacuo
  3. additiona small amount of H2O was added back
  4. additionwas added
  5. concentrationThe mixture was then concentrated in vacuo
  6. customto remove H2O
  7. filtrationsolids were filtered
  8. washwashed with 20% MeOH/DCM
  9. concentrationFiltrate was concentrated in vacuo and residue
  10. filtrationSolids filtered
  11. washwashed with diethyl ether several times
  12. concentrationCombined filtrates were concentrated in vacuo

出典と根拠

ORDレコード
ord-16591df920f746ee895f7de51b177037
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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