Morpholine → 4-Methoxymethyl-5-(4-morpholinylmethyl)-beta-carboline-3-carboxylic acid ethyl ester

HRID 569082Notes

Reaction equation

HRID 569082 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22]O)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].P(Br)(Br)Br.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>ClCCl.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 24614Phosphorus tribromideHCID 138503635-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Product 1

HCID 138503664-Methoxymethyl-5-(4-morpholinylmethyl)-beta-carboline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

5-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester (0.20 g) is dissolved in dichloromethane (5 ml). A solution of phosphorous tribromide (0.17 g) in dichloromethane (3 ml) is added drop by drop with stirring. After three hours of stirring, the mixture is cooled to +10° C. and mixed with a solution of morpholine (1.0 ml) in ethanol (5 ml) drop by drop. After standing overnight the solvent is evaporated, the residue is chromatographed on silica gel with a mixture of dichloromethane (19 parts) and ethanol (1 part) and the title compound (0.16 g) with a melting point of 195°-196° C. is obtained.

Workup

  1. stirringAfter three hours of stirring
  2. temperaturethe mixture is cooled to +10° C.
  3. customthe solvent is evaporated
  4. customthe residue is chromatographed on silica gel with a mixture of dichloromethane (19 parts) and ethanol (1 part)

Sources & evidence

ORD record
ord-b70f9a2eeb924ecb85c8c610d78f3f69
Source dataset
uspto-grants-1988_03
Patent number
US04731365

Reaction notes

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