Acetic Anhydride → HCID 25007099, compound

HRID 1443926Notes

Reaction equation

HRID 1443926 reaction equation
[CH:1]1[C:13]([NH2:14])=[CH:12][C:11]2[CH2:15][CH2:16][CH2:17][N:9]3[C:10]=2[C:2]=1[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=13.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClC(Cl)C>[CH:1]1[C:13]([NH:14][C:18](=[O:20])[CH3:19])=[CH:12][C:11]2[CH2:15][CH2:16][CH2:17][N:9]3[C:10]=2[C:2]=1[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=13

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59168390HCID 59168390, compound

Product 1

HCID 25007099HCID 25007099, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Following the procedure of Example 1, Step 4, 5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-amine (0.10 g, 0.44 mmol), acetic anhydride (0.042 mL, 0.44 mmol) and poly-(4-vinylpyridine) (600 mg) in dichloroethane (15 mL) provided N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-ylacetamide (26 mg). MS (ESI) m/z 269; HPLC purity 99.4% at 210-370 nm, 9.1 min.; 98.4% at 248 nm, 9.1 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 ((Ammon. Form. Buff. pH=3.5/ACN and MeOH) for 10 min, hold 4 min); HRMS: calcd for C17H20N2O+H+, 269.16484; found (ESI, [M+H]+), 269.1646.

Sources & evidence

ORD record
ord-a9e9562a4cb04b2fa961c9edfce8dd7d
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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