Triethylamine → HCID 68922704, compound

HRID 2375256Notes

Reaction equation

HRID 2375256 reaction equation
[NH2:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11].C(N(CC)CC)C.Cl[CH2:20][CH2:21][N:22]([CH2:33][CH2:34]Cl)[S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CN(C)C=O>[CH3:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([N:22]2[CH2:21][CH2:20][N:1]([C@H:2]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:4][C@H:3]3[OH:11])[CH2:34][CH2:33]2)(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 9866743(1S,2R)-(-)-1-Amino-2-indanol

Product 1

HCID 68922704HCID 68922704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 8 g of (1S,2R)-1-aminoindan-2-ol (53.6 mmol) dissolved in 80 ml of dimethylformamide there are added 15 ml of triethylamine (107.2 mmol) and 15.8 g of N,N-bis(2-chloroethyl)-p-toluenesulphonamide (53.6 mmol). The mixture is heated at 80° C. for 24 hours and then the dimethylformamide is evaporated off. The residue is taken up in dichloromethane, washed, dried, filtered and evaporated. The oil obtained is purified by flash chromatography on silica (eluant: dichloromethane/ethyl acetate 95/5) to yield the expected product in the form of a meringue.

Workup

  1. customthe dimethylformamide is evaporated off
  2. washwashed
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe oil obtained
  7. customis purified by flash chromatography on silica (eluant: dichloromethane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-a2b6d3498b9147d58d431f9b326a2601
Source dataset
uspto-grants-2008_12
Patent number
US07465733B2

Reaction notes

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