Triethylamine → (S)-2-(2-(Hydroxymethyl)morpholino)-1-(indolin-1-yl)ethanone

HRID 1524181Notes

Reaction equation

HRID 1524181 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[NH:14]1[CH2:19][CH2:18][O:17][CH:16]([CH2:20][OH:21])[CH2:15]1.C(N(CC)CC)C>C(#N)C>[OH:21][CH2:20][C@@H:16]1[CH2:15][N:14]([CH2:2][C:3]([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][CH2:6]2)=[O:4])[CH2:19][CH2:18][O:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1768971-(2-Chloroacetyl)indoline2×HCID 3497988Morpholin-2-ylmethanol2×

Product 1

HCID 71061264(S)-2-(2-(Hydroxymethyl)morpholino)-1-(indolin-1-yl)ethanoneYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A microwave vial was charged with 1-(chloroacetyl)-indoline (compound 47; 390 mg, 2.00 mmol), hydroxymethylmorpholine (compound 54; 280 mg, 2.39 mmol), triethylamine (0.55 ml, 4.00 mmol) and acetonitrile (2 ml). The vial was sealed and irradiated for 30 min at 100° C. The crude mixture was purified by flash column chromatography (silica, DCM/MeOH 1:0 to 92:8). The product was obtained as a white solid (435 mg; yield 79%).

Workup

  1. customThe vial was sealed
  2. customirradiated for 30 min at 100° C
  3. customThe crude mixture was purified by flash column chromatography (silica, DCM/MeOH 1:0 to 92:8)
  4. customThe product was obtained as a white solid (435 mg; yield 79%)

Sources & evidence

ORD record
ord-65bd49c1fd864c5387fc3d69bf72c2b6
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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