Phenylacetyl chloride → HCID 25006714, compound

HRID 1443914Notes

Reaction equation

HRID 1443914 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]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClC(Cl)C>[CH:1]1[C:9]([NH:10][C:25](=[O:26])[CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[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 7679Phenylacetyl chlorideHCID 59168382HCID 59168382, compound

Product 1

HCID 25006714HCID 25006714, compoundYield 6.6%

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), phenylacetyl chloride (0.058 mL, 0.44 mmol) and poly-(4-vinylpyridine) (600 mg) in dichloroethane (15 mL) provided N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-yl-2-phenylacetamide (10 mg). MS (ESI) m/z 345; HPLC purity 100% at 210-370 nm, 10.6 min.; 100% at 252 nm, 10.6 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 C23H24N2O+H+, 345.19614; found (ESI, [M+H]+), 345.1959.

Sources & evidence

ORD record
ord-046faf7c2c5742f3b24faa64e7ddff4d
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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