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4-Methylmorpholine → HCID 23365866, compound

HRID 1646335
Notes
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Reaction equation

HRID 1646335 reaction equation
Cl[C:2]([O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:3].[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32].CN1CCOCC1>ClCCl>[CH:5]1([O:4][C:2]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[O:3])[CH2:9][CH2:8][CH2:7][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2735892Cyclopentyl chloroformateHCID 23365920Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365866HCID 23365866, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopentyl chloroformate was added to a stirred solution of the amino ester (A) (0.15 g.) and N-methylmorpholine (0.27 g.) in dichloromethane (3 ml.) at 0°-5° C., under an atmosphere of nitrogen. The mixture was stirred for 30 minutes at 0°-5° C., the cooling bath removed, and stirring continued for 1 hour. The mixture was then poured into 1M hydrochloric acid (15 ml.), and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 3:7 v/v ethyl acetate:hexane, to give the title compound (0.18 g., 89%) as a colorless oil; NMR: 1.66 (m, 6 H), 1.82 (m,2 H), 3.83 (s,3 H, CO.OCH3), 3.92 (s,3 H, OCH3), 3.97 (s,2 H, CH2.Ar), 5.04 (m,1 H, --CHO--), 7.09 (m, 3 H), 7.22 (d,1 H), 7.42 (dd,1 H), 7.48 (d,1 H), 7.57 (br,1 H), 9.18 (br,1 H, CONH), 10.57 (s,1 H, H1 -indole).

Workup

  1. customthe cooling bath removed
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. additionThe mixture was then poured into 1M hydrochloric acid (15 ml.)
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated
  8. customThe residual oil was purified by flash chromatography on silica gel (50 ml.)
  9. washeluting with 3:7 v/v ethyl acetate

Sources & evidence

ORD record
ord-7fd60d579c124c54bc2d47071062abde
Source dataset
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05179112

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes