Hydrochloric Acid → HCID 20509736、化合物

HRID 128248ノート

反応式

HRID 128248 の反応式
P(Cl)(Cl)([Cl:3])=O.N(CC1C2C(=CC=CC=2)N(C)C=1)C1C=CC=CC=1.N1CCCC1=O.C(N(CC)CC)C.[N:37]1[CH2:41][CH2:40][CH2:39][C:38]=1[N:42]([CH2:49][C:50]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[N:52]([CH3:59])[CH:51]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl>C(O)C.C1C=CC=CC=1.CCOCC.ClCCCl>[ClH:3].[N:37]1[CH2:41][CH2:40][CH2:39][C:38]=1[N:42]([CH2:49][C:50]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[N:52]([CH3:59])[CH:51]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 20509731N-(3,4-Dihydro-2H-pyrrol-5-yl)-1-methyl-N-phenyl-1H-indole-3-methanamineHCID 20509739HCID 20509739、化合物

生成物 1

HCID 20509736HCID 20509736、化合物

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane溶媒HCID 241Benzene溶媒2 回HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

Phosphorus oxychloride (4.6 g., 0.03 mole), 3-(anilinomethyl)-1-methylindole (7.1 g., 0.03 mole), 2-pyrrolidinone (2.55 g., 0.03 mole) and triethylamine (3.04 g., 0.03 mole) in 75 ml. of 1,2-dichloroethane are reacted according to the procedure of Example 35. The reaction mixture is quenched in 100 ml. of 10% sodium hydroxide and ice and the organic layer separated therefrom. The organic layer is extracted first with 100 ml. of 1.5 N hydrochloric acid and then 100 ml. of water. The combined extracts are washed with ether, made basic with sodium hydroxide, extracted with ether and the ethereal extract dried over magnesium sulfate and concentrated under reduced pressure to provide 6.6 g. of a residual oil which on trituration with ether forms a solid. Crystallization from Skellysolve B yields 4.2 g. of 3-[(N-[1-pyrrolin-2-yl]anilino)methyl]-1-methylindole as the free base, m.p. 95°-97° C. A 2.2 g. sample of the free base is taken up in ethanol and acidified with ethanolic hydrogen chloride and the solution concentrated under reduced pressure. The residue thus obtained is refluxed with benzene permitting the benzene solution to slowly distill. On standing, 1.7 g. of analytically pure 3-[(N-[1-pyrrolin-2-yl]anilino)methyl]-1-methylindole hydrochloride, m.p. 150.5°-154.5° C. (dec.) (corr.) is obtained.

後処理

  1. customThe reaction mixture is quenched in 100 ml
  2. customof 10% sodium hydroxide and ice and the organic layer separated
  3. extractionThe organic layer is extracted first with 100 ml
  4. washThe combined extracts are washed with ether
  5. extractionextracted with ether
  6. extractionthe ethereal extract
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto provide 6.6 g
  10. customCrystallization from Skellysolve B
  11. customyields 4.2 g
  12. concentrationthe solution concentrated under reduced pressure
  13. customThe residue thus obtained
  14. distillationto slowly distill

出典と根拠

ORDレコード
ord-df0646abda1b4900bf029d0ba8b0925b
出典データセット
uspto-grants-1981_03
特許番号
US04259238

反応ノート

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