Acetic Acid → HCID 12017125, compound

HRID 2304532Notes

Reaction equation

HRID 2304532 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:19][CH:7]2[CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 108243-MethoxyanilineHCID 900061-Propyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 12017125HCID 12017125, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4.5 mL (30 mmol) of N-propyl-4-piperidone, 3.4 mL (30 mmol) of m-anisidine, and 1.7 mL (30 mmol) of glacial acetic acid was stirred in 120 mL of 1,2-dichloroethane (DCE) and 9.49 g (45 mmol) of sodium triacetoxyborohydride was added. The solution was stirred at 25° C. for 3 h. The solution was washed with NaHCO3 solution and brine. It was dried and the solvent was evaporated. The m-anisidine excess was distilled off in a Kugelrohr at 100° C./0.05 Torr. There was obtained 3.5 g (47% yield) of N-(3-methoxyphenyl)-1-propyl-4-piperidinamine as a solid. MS m/z=249 (M++H). 300 MHz 1H NMR (CDCl3) δ7.1 (t, 1H); 6.15-6.35 (m, 3H); 3.75 (s, 3H ); 3.25 (m, 1H); 2.9 (m, 2H); 2.3 (m, 2H); 2.15 (m, 4H); 1.5 (m, 4H); 0.9 (t, 3H). Anal calcd. for C15H24N2O; C, 72.54; H, 9.74; N, 11.28. Found: C, 72.55; H, 9.51; N, 11.21.

Workup

  1. washThe solution was washed with NaHCO3 solution and brine
  2. customIt was dried
  3. customthe solvent was evaporated
  4. distillationThe m-anisidine excess was distilled off in a Kugelrohr at 100° C./0.05 Torr

Sources & evidence

ORD record
ord-a12b3695e890444f8e5904df2556a27c
Source dataset
uspto-grants-2002_08
Patent number
US06436959B1

Reaction notes

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