1-Chloroethyl chloroformate → HCID 58772391、化合物

HRID 1361514ノート

反応式

HRID 1361514 の反応式
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])([F:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH3:23])=[C:15]([C:11]2([F:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:20]=1

参加物

4

反応物 2

HCID 5213051-Chloroethyl chloroformateHCID 58772512HCID 58772512、化合物

生成物 1

HCID 58772391HCID 58772391、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-4-fluoro-piperidine 4c (13.8 g, 0.04 mol) in dichloromethane (50 mL) was added 1-chloroethylchloroformate. (7.1 g, 0.05 mol). The mixture was stirred at room temperature for 2 h and then concentrated to dryness. The residual was dissolved in methanol (50 mL) and then heated to reflux for 30 min. The mixture was concentrated to dryness in vacuo, ether was added, the precipitate solid was filtered and washed with ether to obtain 4-(5-chloro-2-methoxyphenyl)-4-fluoropiperidine 4d as its hydrochloride salt. 1H NMR (DMSO-d6): δ 9.10-9.01 (m, 2H), 7.25 (q, J1=8.4 Hz, J2=8.8 Hz, 1H), 7.33 (d, J=2.8 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H), 3.82 (s, 3H), 3.27 (s, 2H), 3.13-3.04 (m, 2H), 2.79-2.66 (m, 2H), 1.924-1.864 (t. 2H). MS (ESI) m/z (M+H+) 243.98.

後処理

  1. concentrationconcentrated to dryness
  2. dissolutionThe residual was dissolved in methanol (50 mL)
  3. temperatureheated
  4. temperatureto reflux for 30 min
  5. concentrationThe mixture was concentrated to dryness in vacuo, ether
  6. additionwas added
  7. filtrationthe precipitate solid was filtered
  8. washwashed with ether

出典と根拠

ORDレコード
ord-f4a90dc2068b499e840f48bb32a729c7
出典データセット
uspto-grants-2011_02
特許番号
US07880007B2

反応ノート

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