Pyridine → 7,15-Diazadispiro[5.1.5.3]hexadecane, 15-(1-oxooctadecyl)-

HRID 435925Notes

Reaction equation

HRID 435925 reaction equation
[CH2:1]1[C:6]2([CH2:16][NH:15][CH2:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:23](Cl)(=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>CCCCCC>[C:23]([N:15]1[CH2:14][C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[NH:7][C:6]2([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5]2)[CH2:16]1)(=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8212Stearoyl chlorideHCID 155578697,15-Diazadispiro[5.1.5~8~.3~6~]hexadecane

Product 1

HCID 6015097,15-Diazadispiro[5.1.5.3]hexadecane, 15-(1-oxooctadecyl)-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

In a 500 ml. 3-necked flask equipped with stirrer, condenser with drying tube, thermometer, dropping funnel and nitrogen inlet was placed a solution of 15.6 g. (0.07 moles) of 7,15-diazadispiro[5,1,5,3]hexadecane in 150 ml. of dry pyridine. Under a dry nitrogen atmosphere, the solution was cooled to 5° C with an external ice bath and a solution of 21.2 g. (0.07 moles) of stearoyl chloride in 50 ml. of hexane was added dropwise with stirring over a 20 minute period. The reaction mixture was then allowed to warm to room temperature and stir for about 16 hours. The reaction mixture was filtered and the filtrate was taken up in ether, washed well with water, then with 2N NaOH solution. The filtrate was again filtered by suction, and the ether solution dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was recrystallized from acetonitrile, yielding colorless crystals, m.p. 56°-59° C.

Workup

  1. custom3-necked flask equipped with stirrer, condenser
  2. customwith drying tube
  3. temperatureto warm to room temperature
  4. stirringstir for about 16 hours
  5. filtrationThe reaction mixture was filtered
  6. washwashed well with water
  7. filtrationThe filtrate was again filtered by suction
  8. dry with materialthe ether solution dried over anhydrous sodium sulfate
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue was recrystallized from acetonitrile
  11. customyielding colorless crystals, m.p. 56°-59° C.

Sources & evidence

ORD record
ord-a69cf8f4b7974094aa8a74c0cceabb8d
Source dataset
uspto-grants-1977_02
Patent number
US04007156

Reaction notes

Loading…