Triethylamine → HCID 53784554, compound

HRID 1788745Notes

Reaction equation

HRID 1788745 reaction equation
[CH3:1][N:2]([CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][C:5]#[C:6][C:7]([CH2:11][CH3:12])(O)[CH2:8][CH3:9].C(N(CC)CC)C.S(Cl)(C)(=O)=O>C(Cl)Cl>[CH3:1][N:2]([CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][C:5]#[C:6][C:7]([CH2:11][CH3:12])=[CH:8][CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13656859HCID 13656859, compound

Product 1

HCID 53784554HCID 53784554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 630 mg N-methyl-N-(1-naphthylmethyl)-5-ethyl-5-hydroxy-3-heptyn-amine in CH2Cl2 are added, dropwise, at -20° 0.5 ml triethylamine and thereafter 0.21 ml mesylchloride, dissolved in CH2Cl2. The mixture is stirred for 3 hours at room temperature, washed several times with water, the organic phase is dried and evaporated. The residue is chromatographed over silica gel (with toluene/ethylacetate 4/1) to give the title compound (Compound 29) as an oil.

Workup

  1. washwashed several times with water
  2. customthe organic phase is dried
  3. customevaporated
  4. customThe residue is chromatographed over silica gel (with toluene/ethylacetate 4/1)

Sources & evidence

ORD record
ord-7529c3f99556424384cd1a0ebf843f7d
Source dataset
uspto-grants-1987_08
Patent number
US04684661

Reaction notes

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