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

HRID 863847Notes

Reaction equation

HRID 863847 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% NaOH, extracted with Et2O 4×, 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% NaOH
  6. extractionextracted with Et2O 4×
  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-0891011ec6634253af13d3c59ba2380f
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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