Sodium Iodide → HCID 67196008, compound

HRID 1013025Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[CH2:9][CH2:8][CH:7]3[CH2:11][CH2:12][CH2:13][CH2:14][CH:6]3[C:5]=2[N:4]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[N:3]=1.Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[H-].[Na+].[I-].[Na+]>CN(C=O)C.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[C:10]2[CH2:9][CH2:8][CH:7]3[CH2:11][CH2:12][CH2:13][CH2:14][CH:6]3[C:5]=2[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:17][CH:16]=2)[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-(3-Methyl-4,5,5a,6,7,8,9,9a-octahydrobenzo[g]indazol-1-yl)phenol (1.49 mmol) was dissolved in N,N′-dimethylformamide (6 mL), and 1-(3-chloropropyl)pyrrolidine (0.22 g, 1.49 mmol), sodium hydride (72 mg, 60% dispersion in mineral oil, 1.79 mmol) and a catalytic amount of sodium iodide were added. The reaction was heated at 70° C. for 3 hours. The solution was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. SiO2 chromatography with 2% triethylamine/10% methanol/ethyl acetate gave 0.268 g of the desired product. LC-MS (C25H35N3O calc'd 393) m/z 394 (M+H). 1H NMR (300 MHz, CDCl3) δ 7.27 (d, J=8.7 Hz, 2H), 6.91 (d, J=9 Hz, 2H), 4.05 (t, J=6.3 Hz, 2H), 2.64 (t, J=7.2 Hz, 2H), 2.58-2.39 (m, 7H), 2.20 (s, 3H), 2.07-2.00 (m, 2H), 1.82-1.10 (m, 14H), 0.91-0.79 (m, 1H).

Workup

extractionextracted with ethyl acetate
dry with materialThe extracts were dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-49181abfd76d4428a4ffc59952f2ac43
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981896B2

Reaction notes

Loading…