Sodium ethoxide → HCID 13281202, compound

HRID 364738Notes

Reaction equation

HRID 364738 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:9][CH2:8][N:7](C=O)[CH2:6][CH2:5]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][CH2:24][CH2:25][CH2:26]N.[O-]CC.[Na+]>C(O)C>[NH:7]1[CH2:6][CH2:5][CH:4]([CH2:3][C:1]2[NH:2][CH2:26][CH2:25][CH2:24][N:23]=2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 12217449HCID 12217449, compoundHCID 13726734HCID 13726734, compound

Product 1

HCID 13281202HCID 13281202, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-cyanomethyl piperidine-1-carboxaldehyde (4. g, 0.026M) and 1,3-diaminopropane mono p-toluenesulfonate (7.3 g, 0.052M) was heated at 100° C. for 1/2 hrs and 200° C. for 2 hrs. The reaction mixture was dissolved in ethanol (50 ml) and sodium ethoxide (0.052M) was added. The mixture was filtered and the filtrate was stripped to dryness and distilled from about 170° to about 190° C./0.2 mmHg to yield 1,4,5,6-tetrahydro-2-[(4-piperidinyl)methyl]-pyrimidine (2.7 g, 56.7% yield). This compound was characterized as dihydrochloride salt, mp 279°-281° C. (EtOH).

Workup

  1. filtrationThe mixture was filtered
  2. distillationdistilled from about 170° to about 190° C./0.2 mmHg

Sources & evidence

ORD record
ord-af3ef6d1a8de48e6a630c282561a12d7
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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