Triethylamine → HCID 22229205, compound

HRID 1838762Notes

Reaction equation

HRID 1838762 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:19](OC1C=CC([N+]([O-])=O)=CC=1)=[O:20].C(N(CC)CC)C.[N:38]1([C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][NH:15][C:19]([N:41]2[CH2:42][CH2:43][N:38]([C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])[CH2:39][CH2:40]2)=[O:20])=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 643495Benzyl piperazine-1-carboxylateHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamate

Product 1

HCID 22229205HCID 22229205, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

At 0° C., 25.0 g (106 mmol) of 4-(tert-butyloxycarbonylaminomethyl)benzylamine in 150 ml of dichloromethane are added dropwise to a solution of 22.4 g (111 mmol) of 4-nitrophenyl chloroformate in 200 ml of dichloromethane, and the mixture is stirred for 10 min. 15.6 ml (111 mmol) of triethylamine are then added dropwise, and the mixture is stirred at RT for 1.5 h. At 0° C., initially 24.5 g (111 mmol) of benzyl piperazine-1-carboxylate in 80 ml of dichloromethane and then 15.6 ml (111 mmol) of triethylamine are added dropwise. The mixture is stirred at RT for 16 h. The solvent is removed from the reaction mixture and the crude product is chromatographed over silica gel (toluene/ethyl acetate=1:1). Crystallization from diisopropyl ether gives 41.7 g of the title compound as a colorless solid of m.p. 108-112° C.

Workup

  1. stirringthe mixture is stirred at RT for 1.5 h
  2. stirringThe mixture is stirred at RT for 16 h
  3. customThe solvent is removed from the reaction mixture
  4. customthe crude product is chromatographed over silica gel (toluene/ethyl acetate=1:1)
  5. customCrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-4bd2ce9341b04b629a38aae1bd9fe8b3
Source dataset
uspto-grants-2004_01
Patent number
US06673786B1

Reaction notes

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