Water → 1-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2one

HRID 46514Notes

Reaction equation

HRID 46514 reaction equation
CN(C)CCN(C)C.C([Li])CCC.C(NC(C)[CH2:19][C:20]1[C:21](=[O:37])[NH:22][CH2:23][CH2:24][CH:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=3)[C:26]=12)(C)C.O>CCCCCC.O1CCCC1>[CH3:19][C:20]1[C:21](=[O:37])[NH:22][CH2:23][CH2:24][CH:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=3)[C:26]=12

Participants

7

Reactant 4

HCID 962WaterHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 128324101-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-oneHCID 178418339Butyllithium

Product 1

HCID 205556141-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The starting material is prepared as follows: 19.2 ml of tetramethyl-ethylenediamine are added under nitrogen to 53.3 ml of 2.4 M n-butyl lithium in hexane at room temperature and the mixture is allowed to react for 15 minutes. Thereupon the solution of 10.9 g of 1-(2-isopropylaminopropyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one in 160 ml of anhydrous tetrahydrofuran is added dropwise. The mixture is refluxed for 30 minutes and subsequently cooled in an ice bath. 120 ml of water are added dropwise and the mixture is stirred with cooling for 30 minutes. The precipitate is collected, washed with water and diethyl ether and dried, to yield the 1-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one melting at 215°-218°.

Workup

  1. customThe starting material is prepared
  2. customto react for 15 minutes
  3. temperatureThe mixture is refluxed for 30 minutes
  4. temperaturesubsequently cooled in an ice bath
  5. temperaturewith cooling for 30 minutes
  6. customThe precipitate is collected
  7. washwashed with water and diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-23b9de7a67a74142be72f03cdea4315f
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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