Dichloromethane → HCID 6917919, compound

HRID 543434Notes

Reaction equation

HRID 543434 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][N:32]([CH3:46])[CH:33]([CH3:45])[CH2:34][CH2:35][C:36]2[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=2I)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(Cl)[Cl:48]>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:48].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][N:32]([CH3:46])[CH:33]([CH3:45])[CH2:34][CH2:35][C:36]2[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=2[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 8058HexaneHCID 10821PhenylacetyleneHCID 20141150HCID 20141150, compoundHCID 178418339Butyllithium

Product 1

HCID 6917919HCID 6917919, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.55 ml (41.4 mmole) of phenylacetylene in 40 ml of dry THF was cooled to 0° and 21.4 ml of 1.9M butyllithium in hexane (41.4 mmole) was added. The resulting solution was stirred for 15 minutes under N2 then transferred to a flask containing 5.53 g (40.6 mmole) of dry ZnCl2. The mixture was stirred 15 minutes at 0° and a solution of 16.33 g (33.8 mmole) of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-iodo-5-methoxy-N,alphadimethylbenzenepropanamine and 0.78 g (0.68 mmoles) of tetrakis(triphenylphosphine)palladium (0) in 100 ml of THF was added. The mixture was allowed to warm to room temperature and stirred for 24 hours. The mixture was diluted with CH2Cl2 and washed with water, 5% HCl, dilute NaOH, dried (K2CO3) and the solvent evaporated in vacuo. The residue was dissolved in MeOH and ethereal hydrogen chloride added. The solvent was evaporated in vacuo and the residue crystallized from 2-propanol/ether. The solid was recrystalled from 2-propanol/ether to give 5.53 g (33% yield) of N-[2-(3,4-dimethoxyphenyl)ethyl]-5-methoxy-N,alphadimethyl-2-(phenyl)ethynyl benzenepropanamine hydrochloride, mp 119°-122° C.

Workup

  1. customthen transferred to a flask
  2. stirringThe mixture was stirred 15 minutes at 0°
  3. stirringstirred for 24 hours
  4. washwashed with water, 5% HCl, dilute NaOH
  5. dry with materialdried (K2CO3)
  6. customthe solvent evaporated in vacuo
  7. dissolutionThe residue was dissolved in MeOH
  8. additionethereal hydrogen chloride added
  9. customThe solvent was evaporated in vacuo
  10. customthe residue crystallized from 2-propanol/ether

Sources & evidence

ORD record
ord-7c811c5acb78465e89418d342f1076c7
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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