Water → HCID 178525079, compound

HRID 1483806Notes

Reaction equation

HRID 1483806 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8](O)=O)[CH2:4][CH2:3]1.[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.[C:19]([O-:22])([O-])=O.[K+].[K+].[OH2:25]>CN(C=O)C>[CH2:17]([N:1]([CH2:17][C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)[C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:22][CH2:19][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:25])[CH2:4][CH2:3]1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 178511567HCID 178511567, compound

Product 1

HCID 178525079HCID 178525079, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of hydrochloride salt of trans-4-aminocyclohexanecarboxylic acid (720 g), BnBr (1700 g, 2.5 eq) and K2CO3 in DMF (8000 mL) was stirred at rt overnight. More BnBr (100 g) was added and the reaction mixture was heated to 50° C. and kept for 3 hrs. The reaction mixture was then poured into water and extracted with EtOAc and combined organic phase washed with brine and concentrated in vacuo to give crude trans-benzyl 4-(dibenzylamino)cyclohexanecarboxylate as white solid (1495 g, 93.9% yield).

Workup

  1. temperaturethe reaction mixture was heated to 50° C.
  2. waitkept for 3 hrs
  3. extractionextracted with EtOAc and combined organic phase
  4. washwashed with brine
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce7633f4435947188848972aefa455ba
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…