Ethyl Acetate → 1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-on-3-yl]-3-[N-methyl-N-(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

HRID 1380895Notes

Reaction equation

HRID 1380895 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:31])[CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[CH:24][CH:25]=2)[CH2:20]1.[C:32](OCC)(=[O:34])C>>[CH3:11][O:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]2[NH:1][C:32](=[O:34])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH3:31])[CH:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][C:23]([O:29][CH3:30])=[CH:24][CH:25]=4)[CH2:20]3)[CH2:13][CH2:12][C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 233245721-[2-(2-Amino-4,5-dimethoxy-phenyl)-ethylamino]-3-[N-methyl-N-(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Product 1

HCID 233245801-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-on-3-yl]-3-[N-methyl-N-(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Procedure

Here, 1-[2-(2-amino-4,5-dimethoxy-phenyl)-ethyl amino]-3-[N-methyl-N-(7-methoxy-1,2,3,4-tetrahydro naphth 2-yl)-amino]-propane (2.0 g, 0.005 mol) and N,N'-carbonyldiimidazole (1 g, 0.006 mol) are reflxed for 60 minutes in absolute ethyl acetate (40 ml). After extraction with saturated potassium carbonate solution and with water, the product which has been evaporated in vacuo is dissolved in methylene chloride and precipitated with petroleum ether. yield: 1.2 g. Mp: 163°-165° C.

Workup

  1. extractionAfter extraction with saturated potassium carbonate solution
  2. customwith water, the product which has been evaporated in vacuo
  3. dissolutionis dissolved in methylene chloride
  4. customprecipitated with petroleum ether

Sources & evidence

ORD record
ord-9d13cc7223db4505b762839e214d95cb
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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