Trifluoroacetic acid → 3-Bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine

HRID 656518ノート

反応式

HRID 656518 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][CH2:10][C:11]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH:5]=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][O:9][CH2:10][C:11]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH:3]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 57557588Tert-butyl 4-(((5-bromopryidin-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

生成物 1

HCID 248009253-Bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine収率 112.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl 4-(((5-bromopryidin-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (100 mg, 0.2 mmoL) in methylene chloride (2 mL) was treated with TFA (0.5 mL). After 1 h, the reaction was concentrated, and the resulting residue was evaporated from methylene chloride (2×). Preparative HPLC afforded 88.0 mg (92%) of the desired compound as its TFA salt. 1H-NMR (CDCl3, 400 MHz) δ 8.65 (s, 1H), 8.52 (s, 1H), 7.84 (s, 1H), 7.24-7.43 (m, 5H), 6.85 (s, br, 1H), 4.46 (s, 2H), 3.45 (s, 2H), 3.33-3.38 (m, 2H), 2.91-2.95 (m, 2H), 2.43-2.48 (m, 2H), 2.22-2.30 (m, 2H). Mass spec.: 362.99 (MH)+.

後処理

  1. concentrationthe reaction was concentrated
  2. customthe resulting residue was evaporated from methylene chloride (2×)

出典と根拠

ORDレコード
ord-29bfde726d0641d98eac599121136b2d
出典データセット
uspto-grants-2011_12
特許番号
US08071778B2

反応ノート

読み込み中…