Formaldehyde → HCID 13081696, compound

HRID 1680174Notes

Reaction equation

HRID 1680174 reaction equation
[CH3:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[CH:6][CH:5]=2.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.O.[CH2:24]=O>C(O)(=O)C>[CH3:11][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]=1[CH2:1][CH2:24][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 31268PyrrolidineHCID 1381803HCID 1381803, compound

Product 1

HCID 13081696HCID 13081696, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 310 g of 2,3-dimethyl-1-phenylindole in 170 ml 40% formaldehyde and 1.6 liters acetic acid there is added dropwise 175 ml pyrrolidine at such a rate that the mixture temperature is 55° to 60°. When the addition is complete the mixture is stirred for 15 minutes and treated at 55° to 60° for 2 hours. 1.6 liters of water are added. The mixture is extracted with toluene (five times 1.6 liters), and the extracts are carefully washed with two 1.6 liter portions of 2 N NaOH. The solution is dried with 100 g of magnesium sulphate and the solvent removed to give 3-methyl-1-phenyl-2-[2-(1-pyrrolidinyl)ethyl]indole as a brown oil which is treated with 7.5 liters of petroleum ether (B.pt. 90°-120°) and then filtered. The petroleum ether solution of 3-methyl-1-phenyl-2-[2(1-pyrrolidinyl)ethyl]indole is treated with hydrogen chloride gas to yield the hydrochloride salt. M.pt. 213°-216°. The free base is set free from the hydrochloride in toluene using 2 N NaOH and obtained as an oil.

Workup

  1. customis 55° to 60°
  2. additionWhen the addition
  3. additiontreated at 55° to 60° for 2 hours
  4. extractionThe mixture is extracted with toluene (five times 1.6 liters)
  5. washthe extracts are carefully washed with two 1.6 liter portions of 2 N NaOH
  6. dry with materialThe solution is dried with 100 g of magnesium sulphate
  7. customthe solvent removed

Sources & evidence

ORD record
ord-c5218d1b06794b4bb1d32d9f7d497b10
Source dataset
uspto-grants-1981_06
Patent number
US04272533

Reaction notes

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