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Morpholine → 4-(3-Bromobenzoyl)morpholine

HRID 1051480
Notes
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Reaction equation

HRID 1051480 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:7])[CH:8]=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8083MorpholineHCID 114563-Bromobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 5319934-(3-Bromobenzoyl)morpholine

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromobenzoic acid (500 mg, 2.49 mmol) in DCM (12 mL) was added morpholine (260 mg, 2.99 mmol), EDCI (1.43 g, 7.47 mmol) and HOBt (1.0 g, 7.47 mmol). The mixture was stirred at room temperature for 4 h. The reaction solution was diluted with water and extracted with DCM. The organic layer was concentrated to give the desired (3-bromophenyl)(morpholino) methanone as a crude product which was used in next step without further purification. LCMS (m/z): 270.1/271.1 [M+H]+/[M+2H]+

Workup

  1. extractionextracted with DCM
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-49835d341552494589f4a4b1a313de51
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388173B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes