Citric Acid → HCID 14403135, compound

HRID 1165828Notes

Reaction equation

HRID 1165828 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:12][CH:11]3[C:13]([CH3:15])([CH3:14])[CH:7]([CH2:8][NH:9][CH2:10]3)[CH2:6]2)[CH2:3][CH2:2]1.[NH2-].[Li+].[C:18]1([CH:24](Br)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:18]1([CH:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:9]2[CH2:8][CH:7]3[C:13]([CH3:15])([CH3:14])[CH:11]([CH2:12][N:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH2:6]3)[CH2:10]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24532Lithium amideHCID 236603BromodiphenylmethaneHCID 14403133HCID 14403133, compound

Product 1

HCID 14403135HCID 14403135, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

1 g 3-cyclopropylmethyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane was dissolved in 25 ml absolute tetrahydrofuran, and 0.2 g lithium amide was added to the solution and stirred for 1 hour at 60° C. and then left to cool. After cooling, a solution of 3 g diphenylmethyl bromide in 25 ml absolute tetrahydrofuran was added slowly in drops, and the reaction mixture was stirred further for 90 min at a temperature of 40° C. Then the reaction mixture was acidified with aqueous citric acid solution and worked up as described in Example 1. 1.5 g 7-diphenylmethyl-3-cyclopropylmethyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane were obtained as an oleaginous base.

Workup

  1. waitleft
  2. temperatureto cool
  3. temperatureAfter cooling
  4. stirringthe reaction mixture was stirred further for 90 min at a temperature of 40° C

Sources & evidence

ORD record
ord-3dfd5eef88dd4e419de26f9988b249d6
Source dataset
uspto-grants-1990_03
Patent number
US04912113

Reaction notes

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