HCID 15296884, compound → HCID 9805027, compound

HRID 863834Notes

Reaction equation

HRID 863834 reaction equation
C([N:20]([CH2:34][CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[O:45][C:46]3[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=3[N:48]=2)=[CH:40][CH:39]=1)[CH2:21][CH2:22][O:23][CH2:24][C:25]#[C:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO.[ClH:56]>C(Cl)Cl.CCO.CO>[ClH:56].[O:45]1[C:46]2[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=2[N:48]=[C:44]1[C:41]1[CH:42]=[CH:43][C:38]([CH2:37][O:36][CH2:35][CH2:34][NH:20][CH2:21][CH2:22][O:23][CH2:24][C:25]#[C:26][C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[CH:39][CH:40]=1

Participants

6

Reactant 2

HCID 15296884HCID 15296884, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 9805027HCID 9805027, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-[3-(4-methylphenyl)-2-propynyloxy]ethanamine (600 mg) is dissolved in a solution of CH2Cl2 (10 ml) and EtOH (10 ml) and is treated with a solution of EtOH/HCl until acidic by pH paper. The solution is concentrated in vacuo, then purified by column chromatography using 5% MeOH/CH2Cl2. The residue is isolated, dissolved in methanol and acidified with acidic methanol. The solution is concentrated to obtain N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-[3-(4-methylphenyl)prop-2-ynyloxy]ethanamine hydrochloride (m.p. 161°-162° C.).

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. custompurified by column chromatography
  3. customThe residue is isolated
  4. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-6c58d62a825e4427abb324128dd0a079
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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