1-Methylpiperazine → 1-(4-Bromo-2-methylbenzoyl)-4-methylpiperazine

HRID 19472

反応式

HRID 19472 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:40]2[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]2)=[O:8])=[C:4]([CH3:11])[CH:3]=1

参加物

6

反応物 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 995704-Bromo-2-methylbenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 593927541-(4-Bromo-2-methylbenzoyl)-4-methylpiperazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

4-Bromo-2-methylbenzoic acid (10 g, 46.5 mmol), and HBTU (23 g, 60.5 mmol) were dissolved in DMF (150 mL), then N-methyl piperazine (6.0 g, 60.5 mmol) and DIPEA (21 mL, 121 mmol) were added. The reaction was stirred overnight before the removal of the DMF in vacuo, the gum was quenched with 2.0N NaOH (100 mL), extracted with diethyl ether (3×200 mL), dried (MgSO4) and solvent removed in vacuo to yield a viscous gum. Purification on silica using 0-10% MeOH in DCM as eluent, gave the title compound as viscous oil. The oil was dissolved in the minimum amount of diethyl ether, iso-hexane was added to give a colourless solid which was filtered and dried (11.8 g, 86%); 1H NMR (CDCl3) 7.40 (s, 1H), 7.36 (d, 1H), 7.04 (d, 1H), 3.86-3.79 (m, 2H), 3.27-3.21 (m, 2H), 2.51-2.45 (m, 2H), 2.32-2.29 (m, 8H); MH+ 298.

後処理

  1. customthe gum was quenched with 2.0N NaOH (100 mL)
  2. extractionextracted with diethyl ether (3×200 mL)
  3. dry with materialdried (MgSO4) and solvent
  4. customremoved in vacuo
  5. customto yield a viscous gum
  6. customPurification on silica using 0-10% MeOH in DCM as eluent

出典と根拠

ORDレコード
ord-737e58edd27a47cbba07fbab19ebb2d9
出典データセット
uspto-grants-2010_06
特許番号
US07745428B2

関連ノート

読み込み中…