Water → HCID 178420349, compound

HRID 556262Notes

Reaction equation

HRID 556262 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:9]([N:8]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@H:5]1[CH2:6][CH2:7][C@H:2]([N:1]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:3][CH2:4]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 178511676HCID 178511676, compound

Product 1

HCID 178420349HCID 178420349, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g (6.8 mmol) of trans-1amino-4-dibenzylaminocyclohexane (see Example 2) is dissolved in 50 mL DMF and stirred for 48 h at RT with 1.6 g (7 mmol) of 1,5-dibromopentane and 2 g of potassium carbonate. The mixture is cooled, combined with water, extracted twice with 100 mL of dichloromethane, dried and the solvent is eliminated in vacuo. The residue is purified over a column (about 100 mL silica gel, about 500 mL ethyl acetate 80/methanol 20+1% concentrated ammonia). The desired fractions are evaporated down in vacuo and crystallised from petroleum ether. Yield: 1.2 g (49%).

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted twice with 100 mL of dichloromethane
  3. customdried
  4. customThe residue is purified over a column (about 100 mL silica gel, about 500 mL ethyl acetate 80/methanol 20+1% concentrated ammonia)
  5. customThe desired fractions are evaporated down in vacuo
  6. customcrystallised from petroleum ether

Sources & evidence

ORD record
ord-49e13281f3a6425aa351dafc000fde45
Source dataset
uspto-grants-2011_11
Patent number
US08058270B2

Reaction notes

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