Hydrochloric Acid → HCID 21491549, compound

HRID 1973458Notes

Reaction equation

HRID 1973458 reaction equation
[CH:1]([NH:4][CH:5]([CH3:8])[CH2:6][NH2:7])([CH3:3])[CH3:2].[Cl:9][C:10]1[CH:25]=[CH:24][C:13]([C:14](=O)[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)=[CH:12][CH:11]=1.O.Cl>C(O)(=O)C>[ClH:9].[CH:1]([NH:4][CH:5]([CH3:8])[CH2:6][N:7]1[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=2[CH:15]=[C:14]1[C:13]1[CH:12]=[CH:11][C:10]([Cl:9])=[CH:25][CH:24]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12270331Cyclohexanone, 2-[2-(4-chlorophenyl)-2-oxoethyl]-HCID 53746371HCID 53746371, compound

Product 1

HCID 21491549HCID 21491549, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.8 g (0.05 mole) of 2-isopropylaminopropylamine are added dropwise to a stirred solution of 12.5 g (0.05 mole) of 2-(p-chloro-phenacyl)cyclohexanone [Example 20(a)] in glacial acetic acid dropwise under nitrogen. After refluxing for 5 hours, the reaction mixture is cooled and poured into 500 ml. of water. The pH is adjusted to 1 with dilute hydrochloric acid, at which point a tan solid separates. This solid is recrystallized from methanol and then twice from an isopropanol-ether mixture to give 1-(2-isopropylaminopropyl)-2-(p-chlorophenyl)-4,5,6,7-tetrahydroindole hydrochloride as tan crystals, m.p. 192°-194° C.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. temperaturethe reaction mixture is cooled
  3. additionpoured into 500 ml
  4. customThis solid is recrystallized from methanol

Sources & evidence

ORD record
ord-8ee7bf42eefd4b4f80eabd1c65b7782a
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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