Hydrochloric Acid → HCID 20509736, compound

HRID 128248Notes

Reaction equation

HRID 128248 reaction equation
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

Participants

11

Reactant 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, compound

Product 1

HCID 20509736HCID 20509736, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 241BenzeneSolvent2×HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-df0646abda1b4900bf029d0ba8b0925b
Source dataset
uspto-grants-1981_03
Patent number
US04259238

Reaction notes

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