Diisopropylamine → Lithium diisopropylamide

HRID 64744Notes

Reaction equation

HRID 64744 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C([Li:12])CCC.[Cl:13][C:14]1[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21])=[CH:16][CH:15]=1.[C:27]1(=[O:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[Cl-].[NH4+]>O1CCCC1>[CH:1]([N-:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li+:12].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH:19]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[C:27]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:25][CH:26]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 7967CyclohexanoneHCID 25517Ammonium ChlorideHCID 136726982-(4-chlorophenoxy)-N,N-dimethylacetamideHCID 178418339Butyllithium

Product 2

HCID 2724682Lithium diisopropylamideHCID 136726991-[(4-Chlorophenoxy)((dimethylamino)carbonyl)methyl]cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Lithium di-isopropylamide was prepared by dissolving di-isopropylamine (11 ml) in tetrahydrofuran (150 ml) followed by the addition of n-butyl lithium (50 ml of 1.7 molar). After 10 minutes stirring, the straw colored liquid was cooled to -78° C. and a solution of 2-(4-chlorophenoxy)-N,N-dimethyl acetamide (16 g, 0.074 mole) in tetrahydrofuran (25 ml) was slowly added. The mixture was stirred for 20 minutes at -78° C. and cyclohexanone (7 ml) added. After 45 minutes at -78° C., the reaction mixture was poured into saturated ammonium chloride solution and a red color ensued. The phases were separated and the organic layer washed with brine, dried over anhydrous potassium carbonate and evaporated giving 1-[(4-chlorophenoxy)((dimethylamino)carbonyl)methyl]cyclohexanol as a red solid. Repeated washing with a cold hexane-isopropanol mixture yielded 2.7 g of a white crystalline solid. Yield: 2.7 g, m.p. 109°-111° C.

Workup

  1. stirringThe mixture was stirred for 20 minutes at -78° C.
  2. waitAfter 45 minutes at -78° C.
  3. customThe phases were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. customevaporated

Sources & evidence

ORD record
ord-cbc7061a8461435687b34c7c5a9e9ee0
Source dataset
uspto-grants-1986_09
Patent number
US04609758

Reaction notes

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