Triethylamine → HCID 68170489, compound

HRID 339299Notes

Reaction equation

HRID 339299 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.COC(OC)OC.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 68170489HCID 68170489, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.182 g (1.00 mmol) of biphenyl-4-carbaldehyde and 0.224 g (1.20 mmol) tert-butyl piperazine-1-carboxylate were dissolved in 10 mL dry DCM. 0.35 mL (3.0 mmol) of trimethylorthoformate and 0.21 mL (1.50 mmol) triethylamine were then added to the reaction mixture at room temperature for 1 hr. The reaction was quenched with a solution of NaHCO3 and diluted with EtOAc. The layers were separated and the aqueous solution extracted with EtOAc 2×. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo to give 0.35 g (100%) of 51 which was used as is for the next reaction.

Workup

  1. customThe reaction was quenched with a solution of NaHCO3
  2. additiondiluted with EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous solution extracted with EtOAc 2×
  5. dry with materialThe organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce4a4e7d179e497ab7bc64756c58b2e8
Source dataset
uspto-grants-2014_11
Patent number
US08894970B2

Reaction notes

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