Chloroacetyl chloride → HCID 18397608, compound

HRID 377442Notes

Reaction equation

HRID 377442 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]([CH:18]([CH3:20])[CH3:19])[C@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[OH:17].C([O-])([O-])=O.[K+].[K+]>ClCCl.O>[Cl:1][CH2:2][C:3]([O:17][C@@H:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@H:8]1[N:7]([CH3:6])[CH:18]([CH3:20])[CH3:19])=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 70184479HCID 70184479, compound

Product 1

HCID 18397608HCID 18397608, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

2.00 grams (17.5 mmol) of chloroacetyl chloride was added drop by drop, in 5 minutes, to a solution of 3.00 grams (14.6 mmol) of (1S,2R)-N-methyl,N-i-propyl-1-amino-2-indanol in 40 ml of dichloromethane at room temperature. The temperature increased to 35° C. The reaction was stirred for 15 hours at room temperature. This was followed by the addition of 50 ml of a 5% K2CO3 solution in water and extraction. The basic water layer was once again extracted using 30 ml of dichloromethane. After the collected organic layers had been washed with water, dried using Na2SO4 and evaporated, 3.96 grams (85%) of product was isolated as a yellow oil. 1H NMR (200 MHz, CDCl3): 1.05 (2*d, 6H), 2.09 (s, 3H), 2.96 (dd, J=8.6 and 3.5 Hz +septet, 2H), 3.14 (dd, J=8.6 and 3.5 Hz, 1H), 3.99 (s, 2H), 4.47 (d, J=3,1 Hz, 1H), 5.47 (dt, J=3,1 and 3.5 Hz, 1H) and 7.10-7.25 (m, 4H). 13C NMR (50.31 MHz, CDCl3): 20.59 (q), 33.00 (q), 37.06 (t), 41.10 (t), 53.61 (d), 66.08 (d), 78.47 (d), 124.84 (d), 125.81 (d), 126.62 (d), 127.61 (d), 138.96 (s), 140.46 (s) and 166.85 (s).

Workup

  1. customat room temperature
  2. extractionThe basic water layer was once again extracted
  3. washAfter the collected organic layers had been washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-243d33b3b6ea477f8bc40d532c5a26c3
Source dataset
uspto-grants-2000_02
Patent number
US06025506

Reaction notes

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