Hydrochloric Acid → 6-(Hydroxymethyl)-N-(2-piperidinoethyl)-3-cyclohexene-1-carboxamide

HRID 566426

Reaction equation

HRID 566426 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C@@H:10]12[C:19](=O)[O:18][C:16](=[O:17])[C@@H:11]1[CH2:12][CH:13]=[CH:14][CH2:15]2.[BH4-].[Na+].Cl>O.CC(O)C>[OH:18][CH2:19][CH:10]1[CH:11]([C:16]([NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:17])[CH2:12][CH:13]=[CH:14][CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33944N-(2-Aminoethyl)piperidineHCID 98495Tetrahydrophthalic anhydride, cis-HCID 4311764Sodium borohydride

Product 1

HCID 212661176-(Hydroxymethyl)-N-(2-piperidinoethyl)-3-cyclohexene-1-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

N-(2-Aminoethyl)piperidine (2.11 g) was added to cis-4-cyclohexene-1,2-dicarboxylic anhydride (2.50 g) and stirred for 6 hours at 140° C. The reaction mixture was suspended into a mixed solution of 2-propanol (125 ml) and water (21 ml) and then sodium borohydride (3.12 g) was added thereto at room temperature. After being stirred for 68 hours at room temperature, the reaction mixture was acidified with dilute hydrochloric acid and then concentrated. The residue was adjusted to pH 9 with saturated sodium hydrogencarbonate aqueous solution and 1N sodium hydroxide, and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate anhydride, and concentrated, thereby yielding a crude (3.34 g) containing the entitled compound as brown syrup.

Workup

  1. customat room temperature
  2. stirringAfter being stirred for 68 hours at room temperature
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydride
  7. concentrationconcentrated
  8. customyielding a crude (3.34 g)

Sources & evidence

ORD record
ord-c1fd2ea043c24870adbe68e0b74e7971
Source dataset
uspto-grants-2001_01
Patent number
US06174885B1

Linked notes

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