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Water → HCID 11719782, compound

HRID 1695520
Notes
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Reaction equation

HRID 1695520 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[C@H:27]1([CH2:37][O:38][C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)[C@@H:36]2[N:31]([CH2:32][CH2:33][CH2:34][CH2:35]2)[CH2:30][CH2:29][CH2:28]1.O>CN(C=O)C>[C@H:27]1([CH2:37][O:38][C:39]2[CH:44]=[CH:43][C:42]([NH:45][C:15]([NH:12][C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:14][CH:13]=3)=[O:16])=[CH:41][CH:40]=2)[C@@H:36]2[N:31]([CH2:32][CH2:33][CH2:34][CH2:35]2)[CH2:30][CH2:29][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8764(4-Aminophenoxy)benzeneHCID 682631,1'-CarbonyldiimidazoleHCID 66879100HCID 66879100, compound

Product 1

HCID 11719782HCID 11719782, compound

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent
3×

Procedure

A solution of 4-phenoxyaniline (185 mg) in DMF (1 ml) was added dropwise to a solution, cooled to 0° C., of carbonyldiimidazole (162 mg) in DMF (1 ml). After 30 minutes, 4-[(1R,9aR)-1-(octahydroquinolizin-1-yl)-methoxy]-phenylamine (289 mg) in DMF (1 ml) was added dropwise. The reaction solution was kept firstly at room temperature for 2 hours and then at 80° C. for 30 minutes. The mixture was added dropwise to water (20 ml), and the resulting precipitate was filtered off with suction and washed with water. Alternatively, the product can also be extracted with ethyl acetate and purified after concentration by chromatography. The product with the molecular weight of 471.60 (C29H33N3O3); MS (ESI): 472 (M+H+) was obtained in this way.

Workup

  1. waitThe reaction solution was kept firstly at room temperature for 2 hours
  2. waitat 80° C. for 30 minutes
  3. filtrationthe resulting precipitate was filtered off with suction
  4. washwashed with water
  5. extractionAlternatively, the product can also be extracted with ethyl acetate
  6. custompurified
  7. concentrationafter concentration by chromatography
  8. customMS (ESI): 472 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-5026103ee0cd4b1984ecbd3fece85763
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163741B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes