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Hydrochloric Acid → 1-[[2-(5-Bromo-3-indolyl)-1,1-dimethylethyl]amino]-3-(2-methylphenoxy)-2-propanol hydrochloride

HRID 2413036
Notes
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Reaction equation

HRID 2413036 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[CH2:8][O:7]1.[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]([CH3:27])([CH3:26])[NH2:25].[ClH:28]>C(#N)C>[ClH:28].[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]([NH:25][CH2:8][CH:6]([OH:7])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[CH3:1])([CH3:26])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13259Indole, 3-(2-amino-2-methylpropyl)-5-bromo-HCID 16640o-CRESYL GLYCIDYL ETHER

Product 1

HCID 126196531-[[2-(5-Bromo-3-indolyl)-1,1-dimethylethyl]amino]-3-(2-methylphenoxy)-2-propanol hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2-Methylphenoxymethyl)oxirane, 4.1 g. (0.025 mole) and 6.65 g. (0.025 mole) of 5-bromo-α,α-dimethyl-1H-indol-3-yl-ethaneamine were mixed and heated at 140° for 1 hr. The mixture was then cooled and dissolved in 40 ml. of acetonitrile while still warm. The product was converted to the hydrochloride salt by treatment of the solution with 5 N ethanolic HCl. The solvent was removed by distillation and the residue dissolved in 30 ml. of acetonitrile. The product crystallized from this solution, yield 11.0 g., m.p. 197°-199°. This material was recrystallized from methanol/isopropanol, yield 8.0 g., m.p. 198.0°-200.0° dec. (corr.).

Workup

  1. temperatureheated at 140° for 1 hr
  2. temperatureThe mixture was then cooled
  3. dissolutiondissolved in 40 ml
  4. customThe solvent was removed by distillation
  5. dissolutionthe residue dissolved in 30 ml
  6. customThe product crystallized from this solution, yield 11.0 g
  7. customThis material was recrystallized from methanol/isopropanol, yield 8.0 g

Sources & evidence

ORD record
ord-00ca0a5347284019b60b9e4027b3a7c9
Source dataset
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04495352

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes