Cyclopentylamine → HCID 19069366, compound

HRID 1781176Notes

Reaction equation

HRID 1781176 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17]1.C([BH3-])#N.[Na+]>CO>[CH:16]1([NH:21][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 661394-PhenoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19069366HCID 19069366, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (5.0 g, 25.1 mmol) and cyclopentylamine (2.5 g, 25 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (1.57 g, 25.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ether, washed with brine, and dried over Na2SO4. The ether was evaporated, and the crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride to provide 5.5 g (83%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 1.31-1.45 (m, 2H), 1.49-1.65 (m, 2H), 1.65-1.80 (m, 3H), 1.81-1.95 (m, 2H), 3.15 (p, J=7.5 Hz, 1H), 3.75 (s, 2H), 6.94-7.04 (m, 4H), 7.05-7.14 (m, 1H), 7.25-7.40 (m, 4H). MS (DCl/NH3) m/e 268 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe ether was evaporated
  5. customthe crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-54dca33b1e734c0db0f0cf1ae93a633a
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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