Hydrochloric Acid → HCID 21266158, compound

HRID 566424

Reaction equation

HRID 566424 reaction equation
[CH2:1]([NH2:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C@@H:16]12[C:25](=O)[O:24][C:22](=[O:23])[C@@H:17]1[CH2:18][CH:19]=[CH:20][CH2:21]2.[BH4-].[Na+].Cl>O.CC(O)C>[OH:24][CH2:25][CH:16]1[CH:17]([C:22]([NH:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:23])[CH2:18][CH:19]=[CH:20][CH2:21]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 16217TetradecylamineHCID 98495Tetrahydrophthalic anhydride, cis-HCID 4311764Sodium borohydride

Product 1

HCID 21266158HCID 21266158, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

1-Tetradecylamine (3.51 g) was added to cis-4-cyclohexene-1,2-dicarboxylic anhydride (2.50 g) and stirred for 5 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 (3.11 g) was added thereto at room temperature. After being stirred for 67.5 hours at room temperature, the reaction mixture was acidified with dilute hydrochloric acid. The resulting solid was collected by filtration under a vacuum, washed with water, and dried, thereby yielding the entitled compound (5.38 g) as white solid.

Workup

  1. customat room temperature
  2. stirringAfter being stirred for 67.5 hours at room temperature
  3. filtrationThe resulting solid was collected by filtration under a vacuum
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-478abe3bf9a9404bbfcca86e0ea2e081
Source dataset
uspto-grants-2001_01
Patent number
US06174885B1

Linked notes

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