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2-Chloro-N,N-dimethylethylamine → Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

HRID 31167
Notes
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Reaction equation

HRID 31167 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10]Cl.[C:13]1([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([OH:29])[CH:25]=3)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C.C(#N)C>[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][O:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[O:20][CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:28][CH2:27]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 212875382-Phenylchroman-6-ol

Product 1

HCID 17978584Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

Cesium carbonate (230 mg) and an excess of 2-(dimethylamino)ethyl chloride in ethyl acetate were added into a solution of 2-phenylchroman-6-ol (150 mg) in acetonitrile (5 ml). The reaction mixture was refluxed for 30 minutes. After removing the solvents, the residue was taken up in water and extracted with ethyl acetate. The combined organic layers were washed with water and then with saturated NaCl-solution and dried with Na2SO4. The dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane. 1H NMR (400 MHz, d6-DMSO) δ: 7.43-7.30 (m, 5H), 6.75-6.67 (m, 3H), 5.03 (dd, 1H, J 10.0, 2.2 Hz), 3.95 (t, 2H, J 5.9 Hz), 2.94 (ddd, 1H, J −16.7, 10.9, 5.8 Hz), 2.69 (ddd, 1H, J −16.7, 5.2, 3.3 Hz), 2.58 (t, 2H, J 5.9 Hz), 2.13 (m, 1H), 1.96 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. customAfter removing the solvents
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialwith saturated NaCl-solution and dried with Na2SO4
  6. customThe dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane

Sources & evidence

ORD record
ord-114c319582744b84bd6f0d497c324daf
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425568B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes