Triethylamine → HCID 68509149, compound

HRID 714123Notes

Reaction equation

HRID 714123 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.ON1C2N=CC=CC=2N=N1.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>ClCCl.O>[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][N:50]([C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:41])[CH3:42]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68509149HCID 68509149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzoic acid (6b) (7 g, 50 mmol) was dissolved in dichloromethane (100 mL), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (10.5 g, 55 mmol), triethylamine (7.7 mL, 55 mmol) and 1-hydroxy-7-azabenzotriazole (HOAt) (7.5 g, 55 mmol) were added successively, stirred for half an hour at room temperature, and then 1-tertbutoxycarbonylpiperazine (6a) (10.2 g, 55 mmol) was added and stirred overnight. On the next day, water was added to quench the reaction. The reaction solution was washed successively with 50 mL saturated sodium bicarbonate solution and saturated sodium chloride solution for three times, the organic phases were concentrated to give 1-tertbutoxycarbonyl-4-(4-fluorobenzoyl)piperazine (6c), 14.8 g white solid (yield 96%). ESI-MS m/z calculated for: 308.15. found: 309.25 [M+H]+.

Workup

  1. stirringstirred overnight
  2. customto quench
  3. customthe reaction
  4. washThe reaction solution was washed successively with 50 mL saturated sodium bicarbonate solution and saturated sodium chloride solution for three times
  5. concentrationthe organic phases were concentrated

Sources & evidence

ORD record
ord-2efc04ef6b6749aca4a647039473f256
Source dataset
uspto-grants-2015_11
Patent number
US09187430B2

Reaction notes

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