HCID 10316830, compound → HCID 131719166, compound

HRID 2211142Notes

Reaction equation

HRID 2211142 reaction equation
O1C=CC2C=CC=C(N3CCN(CCCC(=O)C4C=CC(F)=CC=4)CC3)C1=2.[Br:28][C:29]1[CH:30]=[C:31]([N:39]2[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][Cl:47])[CH2:41][CH2:40]2)[C:32]2[O:37][CH2:36][CH2:35][O:34][C:33]=2[CH:38]=1.[Cl:48]C1C=C(N2CCN(CCCl)CC2)C2OCCOC=2C=1.[Cl:68][C:69]1[CH:70]=[C:71]2[C:76](=[CH:77][CH:78]=1)[C:75](=[O:79])[NH:74][CH2:73][CH2:72]2>>[ClH:47].[ClH:48].[Br:28][C:29]1[CH:30]=[C:31]([N:39]2[CH2:40][CH2:41][N:42]([CH2:45][CH2:46][N:74]3[CH2:73][CH2:72][C:71]4[C:76](=[CH:77][CH:78]=[C:69]([Cl:68])[CH:70]=4)[C:75]3=[O:79])[CH2:43][CH2:44]2)[C:32]2[O:37][CH2:36][CH2:35][O:34][C:33]=2[CH:38]=1

Participants

5

Reactant 4

HCID 10316830HCID 10316830, compoundHCID 19375613HCID 19375613, compoundHCID 19375627HCID 19375627, compoundHCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 131719166HCID 131719166, compoundYield 37%

Procedure

This compound was obtained analogous to the method described in EP-A-0190472 for 1-(benzo-[b]furan-7-yl)-4-[3-(4-fluorobenzoyl)-propyl)piperazine using 1-(7-bromo-2,3-dihydro-1,4-benzodioxin-5-yl)-4-(2-chloroethyl)piperazine (which was prepared similar to the method described for 1-(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)-4-(2-chloroethyl)piperazine as described in EP-A-0190472), and 6-chloro-3,4-dihydroisoquinolin-1(2H)-one. Yield 37%, m.p. <240° C. (dec.), 1H-NMR (DMSO:CDCI3 =4:1)δ3.09 (t, 2H, NCH2CH2Ar J=7 Hz), 3.16 (m, 2H, Hax pipCH2), 3.45 (m, 2H, +NCH2CH2), 3.55 (m, 2H, Heq pipCH2), 3.65-3.75 (cluster, 4H), 3.94 (t, 2H, CH2CH2NC=O), 4.26 (m, 4H, OCH2CH2O), 6.62 (d, 1 H, H-6, J=2 Hz), 6.75 (d, 1H, H-8 J=2 Hz), 7.37 (cluster, 2H), 7.88 (d, 1H, J=8 Hz), 11.0 (br, 1H, NH+)

Workup

  1. customThis compound was obtained analogous to the method
  2. customwas prepared similar to the method

Sources & evidence

ORD record
ord-35e6375a2473419594d3b29562e43eb0
Source dataset
uspto-grants-1995_10
Patent number
US05462942

Reaction notes

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