Acetic Anhydride → 2-(2-Acetamino-phenylsulfanyl)-phenyl-{4(2-(2-acetoxyethoxy)ethyl]piperazin-1-yl}methanone

HRID 251395Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28])[CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37].[C:43](OCC)(=[O:45])[CH3:44]>>[NH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([N:17]1[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:43](=[O:45])[CH3:44])[CH2:21][CH2:22]1)=[O:16])[C:36]([CH3:37])=[O:38]

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 8471Triethylamine

HCID 8857Ethyl Acetate2×

HCID 11338588Quetiapine, open ring-

Product 1

HCID 111559842-(2-Acetamino-phenylsulfanyl)-phenyl-{4(2-(2-acetoxyethoxy)ethyl]piperazin-1-yl}methanone

Procedure

[2-(2-amino-phenylsulfanyl)-phenyl]-{4(2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}methanone (10.7 g, 0.027 mol) was dissolved in ethyl acetate (50 ml) and triethylamine (7.4 ml) was added into reaction mixture. Acetic anhydride (7.6 ml, 0.081 mol) was slowly added to the reaction mixture at room temperature. After 4 h, the reaction mixture was evaporated to give a dark blue oil which was dissolved in ethyl acetate (50 ml) and washed with 2×25 ml saturated NaHCO3 solution and once with brine. The organic phase was evaporated to give a brown oil (10.9 g). The residue of [2-(2-acetamino-phenylsulfanyl)-phenyl-{4(2-(2-acetoxyethoxy)ethyl]-piperazin-1-yl}methanone was used further without purification.

Workup

customthe reaction mixture was evaporated
customto give a dark blue oil which
washwashed with 2×25 ml saturated NaHCO3 solution and once with brine
customThe organic phase was evaporated

Sources & evidence

ORD record: ord-0a4aed533096481791fefbef47eebc41
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863441B2

Reaction notes

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