Benzaldehyde → {4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 1696830Notes

Reaction equation

HRID 1696830 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([O:16][C:17](=[O:33])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][NH2:32])=[CH:25][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:9]([O:16][C:17](=[O:33])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][NH:32][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[CH:25][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59750599Benzyl (4-(4-(2-aminoethoxy)phenyl)butyl)carbamate

Product 1

HCID 58100148{4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Benzyaldehyde (0.74 ml, 7.31 mmol) was added to a solution of 4-[4-(2-aminoethoxy)phenyl]butylcarbamic acid benzyl ester (15) (5.00 g (˜50% purity by NMR), 7.30 mmol) dissolved in anhydrous dichloroethane (50 mL). The resulting solution was stirred at ambient temperature for 7 h. Sodium triacetoxyborohydride (4.10 g, 19.35 mmol) was added slowly and the reduction continued for 60 h. The reaction was quenched with aqueous sodium bicarbonate (50 mL) and then extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed sequentially with water and brine, and dried over anhydrous sodium sulfate. A white solid precipitated out during the drying and collected by dissolving it in dichloromethane and then filtering off the solid sodium sulfate. The filtrate was concentrated and dried under vacuum to give 16 (1.35 g, 43%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.45-1.62 (m, 4H), 2.54 (t, 2H), 3.07-3.22 (m, 4H), 3.88 (s, 2H), 4.10 (t, 2H), 4.73 (br, 1H), 5.09 (s, 2H), 6.79 (d, 2H), 7.04 (d, 2H), 7.28-7.39 (m, 10H); m/z (ESI) 433 [C27H32N2O3+H]+.

Workup

  1. waitthe reduction continued for 60 h
  2. customThe reaction was quenched with aqueous sodium bicarbonate (50 mL)
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe combined organic extracts were washed sequentially with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customA white solid precipitated out during the drying and
  7. customcollected
  8. dissolutionby dissolving it in dichloromethane
  9. filtrationfiltering off the solid sodium sulfate
  10. concentrationThe filtrate was concentrated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-a30260aceb864b0a9df4a8d672121c50
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

Loading…