Morpholine → tert-Butyl4-(3-{2-[3-(4-morpholinylmethyl)phenoxy]ethoxy}-2-pyrazinyl)-1-piperazinecarboxylate

HRID 353710Notes

Reaction equation

HRID 353710 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[O:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[N:12][CH:13]=[CH:14][N:15]=1)=O.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[N:32]1([CH2:1][C:3]2[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=2)[O:6][CH2:7][CH2:8][O:9][C:10]2[C:11]([N:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[CH2:20][CH2:21]3)=[N:12][CH:13]=[CH:14][N:15]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 11304919tert-Butyl4-{3-[2-(3-formylphenoxy)ethoxy]-2-pyrazinyl}-1-piperazinecarboxylate

Product 1

HCID 11271979tert-Butyl4-(3-{2-[3-(4-morpholinylmethyl)phenoxy]ethoxy}-2-pyrazinyl)-1-piperazinecarboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred solution of the aldehyde from step 3 above (71.2 mg, 0.166 mmol) in 1,2-dichloroethane (5 mL) was treated with morpholine (19 mg, 0.22 mmol), 3 Å molecular sieves and sodium triacetoxyborohydride (52 mg, 0.25 mmol). The mixture was stirred at room temperature for 5 h (TLC monitoring). The solution was filtered and the filtrate was treated with an excess of saturated aqueous sodium bicarbonate. The ether extracts were separated and dried over magnesium sulfate. The mixture was filtered and solvent was removed in vacuo to give 54 mg (65%) of the title product as a yellow oil. Pure by NMR. 1H NMR (CDCl3) δ 1.4 (s, 9H); 2.35 (m, 4H); 3.4 (m, 10H); 3.65 (m, 4H); 4.3 (m, 2H); 4.65 (m, 2H); 6.75 (d, 1H); 6.9 (m, 2H); 7.2 (t, 1H); 7.5 (s, 1H); 7.7 (s, 1H).

Workup

  1. filtrationThe solution was filtered
  2. additionthe filtrate was treated with an excess of saturated aqueous sodium bicarbonate
  3. customThe ether extracts were separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-7211cc2d49e4428992066269a2550a3c
Source dataset
uspto-grants-2004_06
Patent number
US06756377B2

Reaction notes

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