Hydrochloric Acid → HCID 20509736, 화합물

HRID 616186노트

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HRID 616186 반응식
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

참가 물질

11

반응물 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, 화합물

생성물 1

HCID 20509736HCID 20509736, 화합물

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 241Benzene용매2회HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

Phosphorus oxychloride (4.6 g., 0.03 mole), 3-(anilino-methyl) -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.

후처리

  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. customas the free base, m.p 95°-97° C
  13. concentrationthe solution concentrated under reduced pressure
  14. customThe residue thus obtained
  15. distillationto slowly distill

출처 및 근거

ORD 기록
ord-84d5538789db4e739a001edbfa8bf0f0
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04072675

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