Ammonia → HCID 23324593, compound

HRID 1380894Notes

Reaction equation

HRID 1380894 reaction equation
[CH3:1][O:2][C:3]1[C:34]([O:35][CH3:36])=[CH:33][C:6]2[C:7](=[O:32])[C:8](=[O:31])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:30])[CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=4)[CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[BH4-].[Na+].Cl.N>CO.O>[OH:32][CH:7]1[C:6]2[CH:33]=[C:34]([O:35][CH3:36])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:30])[CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=3)[CH2:17]2)[C:8]1=[O:31]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 23324574HCID 23324574, compound

Product 1

HCID 23324593HCID 23324593, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Here, 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (0.70 g 0.0014 mol) is dissolved in a mixture of methanol/water=(95:5, 21 ml) then sodium borohydride (0.060 g, 0.0016 mol) is added and the mixture is stirred for 20 minutes at ambient temperature. It is then acidified with hydrochloric acid (2 mol/l), made alkaline with methanolic ammonia and extracted with methylene chloride, dried over magnesium sulphate, concentrated by evaporation and the residue is purified over a column [alumina N (50 g), activity II, eluant: methylene chloride and then with increasing amounts of ethanol (up to 3%)]. The residue is dissolved in acetone and mixed with ethereal hydrochloric acid. The precipitate obtained is suction filtered, washed with ether and dried. Yield: 0.18 g. Mp: 141°-143° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated by evaporation
  4. customthe residue is purified over a column [alumina N (50 g), activity II, eluant
  5. dissolutionThe residue is dissolved in acetone
  6. additionmixed with ethereal hydrochloric acid
  7. customThe precipitate obtained
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-3f9b64d63be8490a9140f9cf1c4f28db
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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