Hydrochloric Acid → HCID 131722816, compound

HRID 1386811Notes

Reaction equation

HRID 1386811 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]2[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH:26](OC)(OC)OC>CCOC(C)=O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]=[CH:26]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 21180792HCID 21180792, compound

Product 1

HCID 131722816HCID 131722816, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 160 mg of N-(3-(1-benzyl-piperidin-4-yl)-propyl)-benzene-1,2-diamine (from Step E) in 4.3 mL of trimethyl orthoformate was added 0. 16 mL concentrated HCl. After stirring at 80° C. for 16 hr, the reaction was diluted with EtOAc and washed with sat'd NaHCO3 solution. Aqueous phase was extracted with 2×20 mL EtOAc. The combined organic phases were washed with brine, dried over MgSO4 and concentrated to give 198 mg of oil, which was used for the next step without further purification.

Workup

  1. washwashed with sat'd NaHCO3 solution
  2. extractionAqueous phase was extracted with 2×20 mL EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1000155f6a32446e9c5ce94b7c06ea8d
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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