Methanol → N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride

HRID 1734683Notes

Reaction equation

HRID 1734683 reaction equation
[ClH:1].[CH2:2](N)[CH3:3].CC[N:7]([CH2:10][CH3:11])[CH2:8][CH3:9].[C:12]1([CH2:18][CH2:19][O:20][CH2:21][CH:22]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:24]([BH3-])#[N:25].[Na+].[CH3:28][OH:29]>C1COCC1>[ClH:1].[O:29]1[C:28]2[CH:14]=[CH:15][CH:16]=[CH:9][C:8]=2[N:7]=[C:10]1[C:11]1[CH:3]=[CH:2][C:18]([CH2:19][O:20][CH2:21][CH2:24][NH:25][CH2:22][CH2:21][O:20][CH2:19][CH2:18][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 162493Acetaldehyde, 2-(2-phenylethoxy)-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 19420744N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol)is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% 15 NaOH, extracted with Et2O 4x, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°- 175° C.).

Workup

  1. customdried
  2. waitAfter 2 hours
  3. customthe reaction mixture is quenched with acetone and 2N HCl
  4. concentrationconcentrated in vacuo to dryness
  5. dissolutionThe residue is dissolved in 3 ml 15% 15 NaOH
  6. extractionextracted with Et2O 4x
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo to dryness
  9. customThe residue is purified by column chromatography
  10. dissolutionThe product is dissolved in EtOH
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-44e205b9ed6340c69d915e0ffa0fbbb9
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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