Triphenylphosphine → tert-butyl 4-{2-[3-(2-chlorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}piperazine-1-carboxylate

HRID 1818844Notes

Reaction equation

HRID 1818844 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][S:9]1(=[O:18])=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:51])([CH3:53])[CH3:52])=[O:48])[CH2:43][CH2:42]2)[S:9]1(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 468330951-(2-Chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 68707981tert-butyl 4-{2-[3-(2-chlorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}piperazine-1-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an analogous manner as general procedure II, step 1, a solution of 1-(2-chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.23 g, 0.8 mmol) in tetrahydrofuran (10 mL) was cooled to 0° C., treated with triphenylphosphine (0.32 g, 1.2 mmol), tert-Butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate (0.37 g, 1.6 mmol) were added followed by diisopropylazodicarboxylate (0.23 mL, 1.2 mmol) to provide tert-butyl 4-{2-[3-(2-chlorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}piperazine-1-carboxylate (0.24 g, 61%) as a white foam:

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-084552488c354a51af22113d674e033e
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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