Acetic Anhydride → HCID 25006712, compound

HRID 1443912Notes

Reaction equation

HRID 1443912 reaction equation
[CH:1]1[C:9]([NH2:10])=[CH:8][C:7]2[CH2:11][CH2:12][N:5]3[C:6]=2[C:2]=1[C:3]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=13.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClC(Cl)C>[CH:1]1[C:9]([NH:10][C:18](=[O:20])[CH3:19])=[CH:8][C:7]2[CH2:11][CH2:12][N:5]3[C:6]=2[C:2]=1[C:3]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=13

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59168382HCID 59168382, compound

Product 1

HCID 25006712HCID 25006712, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Following the procedure of Example 1, Step 4, 4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indole-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 28 mg of N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-ylacetamide. MS m/z 269; HPLC purity 100% at 210-370 nm, 9.2 min.; 98.7% at 248 nm, 9.2 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]+), 269.1651.

Sources & evidence

ORD record
ord-147fc16117e14549bb7dab747a4775c1
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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