Triethylamine → 3-Methoxycarbonylethylcarbonyloxy-1-phenylindole hydrochloride

HRID 1194397Notes

Reaction equation

HRID 1194397 reaction equation
[ClH:1].C(N(CC(O)CNC([C:13]1[N:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)CC)C.C(N(CC)CC)C.[Cl-].[CH3:38][O:39][C:40](=[O:46])[CH2:41][CH2:42][C:43](O)=[O:44]>C(Cl)Cl>[ClH:1].[CH3:38][O:39][C:40]([CH2:41][CH2:42][C:43]([O:22][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:13]=1)=[O:44])=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 547241132-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-hydroxy-1-phenylindole hydrochlorideHCID 86605420Succinic acid methylester chloride

Product 1

HCID 867428213-Methoxycarbonylethylcarbonyloxy-1-phenylindole hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g of 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-hydroxy-1-phenylindole hydrochloride (0.005 mole) are mixed in 25 ml of methylene chloride with 0.7 ml triethylamine (0.005 mole) and 0.6 ml of succinic acid methylester chloride and the reaction mixture agitated for 1 h at room temperature. The solution is then washed with a saturated solution of sodium chloride, dried over sodium sulfate, filtered and evaporated. The residue is purified by low pressure chromatography using methylene chloride as the elution agent, as described in Example 3. 2-[3-N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxycarbonylethylcarbonyloxy-1-phenylindole hydrochloride is obtained as an oily product.

Workup

  1. washThe solution is then washed with a saturated solution of sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by low pressure chromatography

Sources & evidence

ORD record
ord-d81c6409718e4dbbaa0a27e706b50e8a
Source dataset
uspto-grants-1989_03
Patent number
US04814345

Reaction notes

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