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Triethylamine → 3-(3-Morpholin-4-ylmethyl-phenyl)-acrylic Acid Ethyl Ester

HRID 1064180
Notes
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Reaction equation

HRID 1064180 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH:23]=[CH2:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:27]([O:26][C:22](=[O:25])[CH:23]=[CH:24][C:2]1[CH:14]=[CH:13][CH:12]=[C:4]([CH2:5][N:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[CH:3]=1)[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 177503184-(3-Iodobenzyl)morpholine

Product 1

HCID 724065063-(3-Morpholin-4-ylmethyl-phenyl)-acrylic Acid Ethyl EsterYield 80%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(3-iodo-benzyl)-morpholine (3.44 g, 11.4 mmol) in N,N-dimethylformamide (20 mL) was added triethylamine (1.7 mL, 12.5 mmol), ethyl acrylate (4.1 mL, 45.4 mmol), tri-o-tolylphosphine (346 mg, 1.14 mmol) and palladium (II) acetate (127 mg, 0.57 mmol). The mixture was heated at 80° C. overnight. After concentration, the mixture was chromatographed on silica gel to afford Intermediate 172(a) as a colorless oil (2.37 g, 9.1 mmol) in 80% yield.

Workup

  1. concentrationAfter concentration
  2. customthe mixture was chromatographed on silica gel

Sources & evidence

ORD record
ord-861aa3cc54064dd497bd5c39d197b2e2
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06967198B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes