1H-Indole-3-propanoic acid → N-(4-Dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)propionamide hydrochloride

HRID 346790

反応式

HRID 346790 の反応式
NCC1CCC(N(C)C)(C2C=CC=CC=2)CC1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.N1C2C(=CC=CC=2)C(CCC(O)=O)=C1.[CH3:50][N:51]([CH3:79])[C:52]1([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[CH2:57][CH2:56][CH:55]([CH2:58][NH:59][C:60](=[O:72])[CH:61]([C:63]2[C:71]3[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=3)[NH:65][CH:64]=2)[CH3:62])[CH2:54][CH2:53]1.[Cl:80][Si](C)(C)C>CC(=O)CC.CO>[ClH:80].[CH3:79][N:51]([CH3:50])[C:52]1([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[CH2:57][CH2:56][CH:55]([CH2:58][NH:59][C:60](=[O:72])[CH:61]([C:63]2[C:71]3[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=3)[NH:65][CH:64]=2)[CH3:62])[CH2:54][CH2:53]1

参加物

8

反応物 5

HCID 37441H-Indole-3-propanoic acidHCID 6397ChlorotrimethylsilaneHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 9980646N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)propionamideHCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine

生成物 1

HCID 9980645N-(4-Dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)propionamide hydrochloride

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

The non-polar diastereoisomer of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (232 mg, 1.0 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (415 mg, 1.5 mmol.) were added to a solution of 3-(1H-indol-3-yl)propionic acid (189 mg, 1.0 mmol.) in abs. methanol, and stirring was carried out for 20 h at RT. For working up, the mixture was concentrated, the residue was taken up in water (10 ml) and ether (10 ml), and the phases were separated. The aqueous phase was adjusted to pH 11 with 5M NaOH and extracted with EE (4×10 ml). The combined organic extracts were washed with 1M NaOH (2×3 ml), dried, filtered and concentrated. For the preparation of the hydrochloride, the resulting non-polar diastereoisomer of N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)propionamide (220 mg, 0.54 mmol.) was dissolved in 2-butanone; chlorotrimethylsilane (104 μl, 0.82 mmol.) was added thereto, and stirring was carried out for 1 h at RT. After 1 h at 4° C., the resulting precipitate was filtered off with suction, washed with cold 2-butanone (1 ml) and cold ether (2×1 ml) and dried in vacuo. The target compound was obtained in a yield of 168 mg (colourless solid, m.p. 163–168° C. with decomposition).

後処理

  1. concentrationthe mixture was concentrated
  2. customether (10 ml), and the phases were separated
  3. extractionextracted with EE (4×10 ml)
  4. washThe combined organic extracts were washed with 1M NaOH (2×3 ml)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customFor the preparation of the hydrochloride
  9. waitwas carried out for 1 h at RT
  10. waitAfter 1 h at 4° C.
  11. filtrationthe resulting precipitate was filtered off with suction
  12. washwashed with cold 2-butanone (1 ml) and cold ether (2×1 ml)
  13. customdried in vacuo
  14. customThe target compound was obtained in a yield of 168 mg (colourless solid, m.p. 163–168° C. with decomposition)

出典と根拠

ORDレコード
ord-26cc5f7d9a1e44df8fee5daf1b530e31
出典データセット
uspto-grants-2007_02
特許番号
US07173045B2

関連ノート

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