Diisopropylethylamine → HCID 21446145, compound

HRID 597739Notes

Reaction equation

HRID 597739 reaction equation
ClCCC([N:6]1[CH2:11][CH2:10][CH2:9][C:8]2([CH2:16][CH:15]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH2:14]3)[CH2:7]1)=O.N1C(=O)CCC2(CC3CC2CC3)C1=O.C(N(C(C)C)CC)(C)C>C1C=CC=CC=1>[NH:6]1[CH2:11][CH2:10][CH2:9][C:8]2([CH2:16][CH:15]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH2:14]3)[CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21446160HCID 21446160, compoundHCID 21446167HCID 21446167, compound

Product 1

HCID 21446145HCID 21446145, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.8 g (0.0178 mole) of 1'-(3-chloropropionyl)-spiro[bicyclo[2.2.2]octane-2,3'-piperidine] is dissolved in 50 ml of abs. benzene; an addition is then made of 3.0 g (0.018 mole) of (1RS, 2RS, 4SR)-spiro[norbornane-2,3'-piperidine] (see Example 2) and 3.5 g (0.0267 mole) of diisopropylethylamine, and the whole refluxed in a nitrogen atomosphere, with stirring, for 42 hours. The mixture is concentrated in vacuo under 12 Torr, and the residue distributed between 50 ml each of water and of chloroform. After separation of the chloroform extract, the aqueous phase is subsequently extracted again with 50 ml of chloroform. The chloroform extracts are washed separately twice with 50 ml of water each time; they are then dried over sodium sulphate and concentrated in vacuo (ca. 12 Torr). There is thus obtained crude 1'-[3-(1RS,2RS,4SR)-spiro[norbornane-2,3'-piperidin]-1' -yl)-propionyl]-spiro[bicyclo[2.2.2]octane-2,3'-piperidine] as colourless oil.

Workup

  1. additionan addition
  2. temperaturethe whole refluxed in a nitrogen atomosphere
  3. concentrationThe mixture is concentrated in vacuo under 12 Torr
  4. customAfter separation of the chloroform
  5. extractionextract
  6. extractionthe aqueous phase is subsequently extracted again with 50 ml of chloroform
  7. washThe chloroform extracts are washed separately twice with 50 ml of water each time
  8. dry with materialthey are then dried over sodium sulphate
  9. concentrationconcentrated in vacuo (ca. 12 Torr)

Sources & evidence

ORD record
ord-283c5c1470c64e3ab09e5e27dd6d1241
Source dataset
uspto-grants-1977_03
Patent number
US04015007

Reaction notes

Loading…