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2-Morpholinoethylamine → HCID 18945158, compound

HRID 399829
Notes
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Reaction equation

HRID 399829 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[CH:9]=[C:10]([CH:15]=2)[C:11]([O:13]C)=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.[NH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[N:23]1([CH2:22][CH2:21][NH:20][C:11](=[O:13])[C:10]2[CH:15]=[C:6]([N:1]3[CH:2]=[CH:3][CH:4]=[CH:5]3)[CH:7]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[CH:9]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 189451711,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylate

Product 1

HCID 18945158HCID 18945158, compoundYield 25.6%

Conditions

Temperature
120 °C

Procedure

A mixture of dimethyl 5-(pyrrol-1-yl)isophthalate (1.0 g) and 4-(2-aminoethyl)morpholine (0.65 g) was heated at 120° C. for 2 hours. The residue was purified by column chromatography on silica gel (50 g) with chloroform-methanol (30:1) as an eluent. The fractions containing object product were combined and evaporated in vacuo. The crystalline residue was recrystallized from ethanol-ether to afford N-[2-(morpholin-4-yl)ethyl]-3-methoxycarbonyl-5-(pyrrol-1-yl)benzamide (353 mg).

Workup

  1. customThe residue was purified by column chromatography on silica gel (50 g) with chloroform-methanol (30:1) as an eluent
  2. additionThe fractions containing object product
  3. customevaporated in vacuo
  4. customThe crystalline residue was recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-6b1da12103874149adfb9626cd3e77ce
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05824691

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes