3-Chloro-N,N-dimethyl-1-propanamine → HCID 3067726, compound

HRID 1388543Notes

Reaction equation

HRID 1388543 reaction equation
CN(C)C[CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.C([Li])CCC.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29]CCl>CCOCC.CCCCCC>[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2

Participants

6

Reactant 3

HCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 3067724HCID 3067724, compoundHCID 178418339Butyllithium

Product 1

HCID 3067726HCID 3067726, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A solution of 3.10 g 11H-dibenzo(b,e)-1,4-dithiepin (of example 14, reference given) in 50 ml of ether was stirred and treated dropwise with 10 ml of 15% n-butyllithium solution in hexane for 15 minutes in a nitrogen atmosphere. The mixture was stirred for another 30 minutes at room temperature. It was then treated dropwise with 10 ml of 3-dimethylaminopropyl chloride, the mixture stirred for 4 hours and washed with water. The basic product was then extracted with dilute hydrochloric acid, the acid layer made alkaline with aqueous ammonia and the base extracted with ether. Processing of the extract yielded 3.7 g for oily base which was chromatographed on a column of 200 g neutral of aluminium oxide (activity II). A small amount of less polar impurities was initially eluted with benzene which then eluted 2.89 g of a homogeneous oily base which was converted by neutralization with oxalic acid to the hydrogen oxalate, m.p. 181°-182° C. (ethanol).

Workup

  1. stirringthe mixture stirred for 4 hours
  2. washwashed with water
  3. extractionThe basic product was then extracted with dilute hydrochloric acid
  4. extractionthe base extracted with ether
  5. customProcessing of the extract yielded 3.7 g for oily base which
  6. customwas chromatographed on a column of 200 g neutral of aluminium oxide (activity II)
  7. washA small amount of less polar impurities was initially eluted with benzene which
  8. washthen eluted 2.89 g of a homogeneous oily base which

Sources & evidence

ORD record
ord-ee332f1b403b4efc8a4c7f2552436993
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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