Diisopropylethylamine → HCID 21842573, compound

HRID 1737449Notes

Reaction equation

HRID 1737449 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([CH2:11][S:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]2=3)[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.Br[CH2:26][CH2:27][CH2:28][CH:29]([C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([Cl:48])[CH:43]=1)[CH2:30][N:31]([CH3:41])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:48][C:44]1[CH:43]=[C:42]([CH:29]([CH2:28][CH2:27][CH2:26][N:2]2[CH2:7][CH2:6][C:5]3([CH2:11][S:10][C:9]4[CH:12]=[CH:13][CH:14]=[CH:15][C:8]3=4)[CH2:4][CH2:3]2)[CH2:30][N:31]([CH3:41])[S:32]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 21842622HCID 21842622, compoundHCID 70028544Spiro(benzo[b] thiophene-3(2H),4'-piperidine) hydrochloride

Product 1

HCID 21842573HCID 21842573, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
52 °C

Procedure

Spiro(benzo[b] thiophene-3(2H),4'-piperidine) hydrochloride (16.5 mg, 0.068 mmol) and N,N-diisopropylethylamine (0.036 mL, 27 mg, 0.21 mmol) were added to a solution of N-(5-bromo-2-(3-chlorophenyl)pentyl)-N-methylbenzenesulfonamide (24.6 mg, 0.057 mmol) in 0.30 mL of acetonitrile, and the mixture was heated in an oil bath at 52° C. After 2 days, tetrabutylammonium iodide (5.5 mg, 0.011 mmol) was added and the reaction was continued for an additional 24 h. Without work-up, the reaction mixture was purified by preparative TLC. Elution with 30% ethyl acetate in dichloromethane gave 13.5 mg the title compound. 1NMR (400 MHz, CD3OD): δ 7.74 (d, 2H, J=8 Hz), 7.64 (tt, 1H, J=8, 1 Hz), 7.57 (t, 2H, J=8 Hz), 7.33-7.22 (m, 3H), 7.18 (d, 1H, J=8 Hz), 7.13-7.01 (m, 4H), 3.32-3.25 (m, 3H), 3.11 (dd, 1H, J=13, 8 Hz), 3.00-2.84 (m, 3H), 2.61 (s, 3H), 2.48-2.35 (m, 2H), 2.21 (bq, 2H, J=12 Hz), 1.99 (tt, 2H, J=13, 4 Hz), 1.84-1.75 (m, 3H), 1.67-1.56 (m, 1H), 1.52-1.34 (m, 2H). Mass spectrum (ESI): m/z=555 (M+1).

Workup

  1. waitthe reaction was continued for an additional 24 h
  2. customWithout work-up, the reaction mixture was purified by preparative TLC
  3. washElution with 30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-e4d0ece3fd7e4879bb5569601ecfa37f
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

Loading…