Hydrochloric Acid → HCID 21491591, compound

HRID 1973464Notes

Reaction equation

HRID 1973464 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:12](=O)[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O.O.Cl>C(O)(=O)C>[ClH:8].[CH:1]([NH:4][CH2:5][CH2:6][N:7]1[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=2[CH:13]=[C:12]1[C:11]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:9]([Cl:8])[CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 88098N-IsopropylethylenediamineHCID 12270332Cyclohexanone, 2-[2-(3,4-dichlorophenyl)-2-oxoethyl]-

Product 1

HCID 21491591HCID 21491591, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.9 g (0.028 mole) of isopropylaminoethylamine are added dropwise to a stirred solution of 8.0 g (0.028 mole) of 2-(3,4-dichlorophenacyl)cyclohexanone in glacial acetic acid under nitrogen. After refluxing for 5 hours, ice and water are added and the pH of the aqueous solution is adjusted to 1 with dilute hydrochloric acid. The aqueous solution is washed with ether. The aqueous phase is made basic with sodium carbonate and extracted with ether. The ether solution is dried over sodium sulfate and concentrated to off-white solid, which is recrystallized twice from a methanol-ether mixture to give 1-(2-isopropylaminoethyl)-2-(3,4-dichlorophenyl)-4,5,6,7-tetrahydroindole hydrochloride as crystals, m.p. 207°-210° C.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. washThe aqueous solution is washed with ether
  3. extractionextracted with ether
  4. dry with materialThe ether solution is dried over sodium sulfate
  5. concentrationconcentrated to off-white solid, which
  6. customis recrystallized twice from a methanol-ether mixture

Sources & evidence

ORD record
ord-e43bbad108654b619044d7506c3c9854
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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