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Ethanolamine → N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

HRID 861439
Notes
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Reaction equation

HRID 861439 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:30])[CH2:28]Br)=[CH:23][N:22]=1.[BH4-].[Na+].C(CN)O>C(#N)C.C(OCC)(=O)C.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:28][CH:27]([OH:30])[C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[N:22][CH:23]=2)[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 700EthanolamineHCID 411116alpha-(3,4-Dimethoxyphenyl)benzeneethanamineHCID 4311764Sodium borohydrideHCID 194329212-Bromo-1-(6-chloropyridin-3-YL)ethanone

Product 1

HCID 19704231N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

Reagents, catalysts & solvents 3

HCID 702
Ethanol
Solvent
HCID 6342AcetonitrileSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of α-(3,4-dimethoxyphenyl)-benzenee-thanamine (see Washburn et al., EP 0 659 737 A2 for the preparation of this compound) (257 mg, 1 mmol, 2 eq) in anhydrous acetonitrile (10 mL) is added a solution of 2-chloro-5-(2-bromoacetyl)pyridine (prepared as described in Example 3) (111 mg, 0.5 mmol) at 0° C. under a nitrogen atmosphere. The mixture is allowed to warm to room temperature and stirred for 1 h. To this mixture is added a solution of sodium borohydride (110 mg, 2.9 mmol, 5.8 eq) in abs. ethanol at room temperature. After one hour, the excess sodium borohydride is quenched with 1N HCl to pH 4.0 and then ethanol amine (0.28 mL, 4.5 mmol, 8 eq) is added. After stirring for 10 minutes, the mixture is diluted with ethyl acetate (30 mL). The organic layer is washed with brine, dried over anhydrous sodium sulfate and then concentrated. Purification by silica column gives the desired compound.

Workup

  1. customat room temperature
  2. waitAfter one hour
  3. customthe excess sodium borohydride is quenched with 1N HCl to pH 4.0
  4. stirringAfter stirring for 10 minutes
  5. washThe organic layer is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customPurification by silica column

Sources & evidence

ORD record
ord-b87efb50b82d4c2b82c971c04f44b5c5
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05714506

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes