Sodium ethoxide → HCID 13281202, compound

HRID 485813Notes

Reaction equation

HRID 485813 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°-28° 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-ebe9a8578bca415a85f310cb87e8f85f
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

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