Isopropylamine → HCID 53827166, compound

HRID 1764143Notes

Reaction equation

HRID 1764143 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:12]1([C:18]2[CH:33]=[CH:32][C:21]([O:22][CH:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:24](Cl)=[O:25])=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1>O1CCCC1>[CH:1]([NH:4][C:24](=[O:25])[CH:23]([O:22][C:21]1[CH:32]=[CH:33][C:18]([C:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=2)=[CH:19][CH:20]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 54077320HCID 54077320, compound

Product 1

HCID 53827166HCID 53827166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5 g of isopropylamine and 5 ml of triethylamine in 100 ml of absolute tetrahydrofuran is slowly added dropwise with stirring at -5° C a solution of 13 g of α-[p-(1-cyclohexenyl)-phenoxy]-heptanoic acid chloride in 25 ml of absolute tetrahydrofuran. The reaction mixture is left to stand for 5 hours at room temperature, then evaporated in vacuo to dryness. The residue is partitioned between methylene chloride and 2N hydrochloric acid. The organic phase is washed with saturated sodium bicarbonate solution and water, dried over sodium sulphate and evaporated in vacuo. The residue yields the crude α-[p-(1-cyclohexenyl)-phenoxy]-heptanoic acid isopropylamide of the formula ##STR23## (m.p. 86°-88° C after recrystallisation from petroleum ether).

Workup

  1. waitThe reaction mixture is left
  2. customevaporated in vacuo to dryness
  3. customThe residue is partitioned between methylene chloride and 2N hydrochloric acid
  4. washThe organic phase is washed with saturated sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0ddebb94115046419fc6b3f78c445f31
Source dataset
uspto-grants-1978_09
Patent number
US04115416

Reaction notes

Loading…