Benzaldehyde → 1-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-benzyl-2-imidazolidinone, hydrochloride

HRID 369764Notes

Reaction equation

HRID 369764 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][NH:22][C:21]4=[O:25])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.O1C2C=CC=C(N3CCNCC3)C=2OCC1.[Cl:42]CCCN1CCNC1=O.[CH:52](=O)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[BH4-].[Na+]>C(O)(=O)C.C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>[ClH:42].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][N:22]([CH2:52][C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)[C:21]4=[O:25])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 240Benzaldehyde2×HCID 65853EltoprazineHCID 4311764Sodium borohydride2×HCID 150064211-(3-Chloropropyl)imidazolidin-2-oneHCID 232826641-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-2-imidazolidinone

Product 1

HCID 1317206581-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-benzyl-2-imidazolidinone, hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 22328969EtOH ethyl acetate triethylamineSolvent

Procedure

A solution of 1-[3-[4-(1,4-benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-2-imidazolidinone (prepared from 1-(1,4-benzodioxan-5-yl)piperazin and 1-(3-chloro-1-propyl)-2-imidazolidinone by the method described in EXAMPLE 2) (2.5 g) and benzaldehyde (2.3 g) in glacial acetic acid (30 ml) was treated portionwise with sodium borohydride (0.6 g) keeping the temperature at 10° C. After stirring for 40 min. at room temperature additional benzaldehyde (2.3 g) and sodium borohydride (0.6 g) was added and the mixture stirred for 16 h at room temperature. Removal of solvent in vacuo gave a heavy oil which was applied to a silica gel column (eluent: ethyl acetate/ethanol/triethylamine=10:1:1). The title compound was isolated as a viscous oil which crystallized as the hydrochloride from an acetone/ether mixture by addition of an ether solution of dry HCl. Yield: 2.8 g, mp: 181-91° C. 1H NMR (δ, DMSO): 1.90-2.10 (m, 2H), 3.00-3.25 (m, 10H), 3.30 (t, 2H), 3.35-3.65 (m, 4H), 4.20 (s, 4H), 4.25 (s, 2H), 6.50 (d, 1H), 6.55 (d, 1H), 6.75 (t, 1H), 7.00 (b, 2H), 7.20-7.40 (m, 5H).

Workup

  1. customat 10° C
  2. additionwas added
  3. customRemoval of solvent in vacuo
  4. customgave a heavy oil which

Sources & evidence

ORD record
ord-6ff11964173745ec931ced3cb706d291
Source dataset
uspto-grants-2000_10
Patent number
US06140331

Reaction notes

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