HCID 57514177、化合物 → 2-(3-bromophenyl)-N1-methylpropan-1,2-diamine

HRID 73263ノート

反応式

HRID 73263 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:13]C(=O)OC(C)(C)C)([CH3:12])[CH2:9][NH:10][CH3:11])[CH:5]=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:13])([CH3:12])[CH2:9][NH:10][CH3:11])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 57514177HCID 57514177、化合物

生成物 1

HCID 673044282-(3-bromophenyl)-N1-methylpropan-1,2-diamine収率 76%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

tert-Butyl 2-(3-bromophenyl)-1-(methylamino)propan-2-ylcarbamate (CD3; R1=Me, R4=Me) (0.62 g, 1.8 mmol) was dissolved in 25% TFA in DCM (25 mL) and the mixture was left stirring at RT for 1 h. The mixture was concentrated in vacuo and the residue was redissolved in CHCl3 (20 mL). The solution was washed with 15% NaOH (10 mL) and the aqueous layer was extracted with CHCl3 (3×10 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 0.33 g (76%) of crude 2-(3-bromophenyl)-N1-methylpropan-1,2-diamine as a colorless oil. 1H NMR (CDCl3) δ 7.65 (t, J=1.7 Hz, 1H), 7.41-7.34 (m, 2H), 7.21 (t, J=7.8 Hz, 1H), 2.86 (dd, J=11.7, 0.6 Hz, 1H), 2.64 (dd, J=11.7, 0.6 Hz, 1H), 2.38 (s, 3H), 1.54 (bs, 3H), 1.43 (s, 9H). MS (ESI) m/e 242.9 (M+H)+. The compound was used in the next step without further purification.

後処理

  1. waitthe mixture was left
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was redissolved in CHCl3 (20 mL)
  4. washThe solution was washed with 15% NaOH (10 mL)
  5. extractionthe aqueous layer was extracted with CHCl3 (3×10 mL)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c4e16d023d2b44fd87c9868d390b9d76
出典データセット
uspto-grants-2014_09
特許番号
US08829036B2

反応ノート

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