Hexanoyl chloride → HCID 25006718, compound

HRID 1443924Notes

Reaction equation

HRID 1443924 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](Cl)(=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>ClCCl>[CH:1]1[C:13]([NH:14][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[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 67340Hexanoyl chlorideHCID 59168390HCID 59168390, compound

Product 1

HCID 25006718HCID 25006718, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (0.13 g, 0.55 mmol), hexanoyl chloride (0.076 mL, 0.55 mmol) and poly-(4-vinylpyridine) (500 mg) in dichloromethane (12 mL) provided N-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-ylhexanamide (14 mg). MS (ES) m/z 325.1; HPLC purity 100% at 210-370 nm, 11.0 min.; 98.9% at 250 nm, 11.0 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 C21H28N2O+H+, 325.22744; found (ESI, [M+H]+), 325.2289.

Sources & evidence

ORD record
ord-a93ccc842ad741acb8256f60820bf5ca
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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