Ethanol → HCID 13749188, compound

HRID 1732074Notes

Reaction equation

HRID 1732074 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][C:14]([CH3:22])([CH3:21])[CH:15]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:7]1=[C:6]2[CH3:23].B(Br)(Br)[Br:25].C(O)C.CCOCC>C(Cl)(Cl)Cl>[BrH:25].[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][C:14]([CH3:21])([CH3:22])[CH:15]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:7]1=[C:6]2[CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 13749156HCID 13749156, compound

Product 1

HCID 13749188HCID 13749188, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6,7,8,9-tetrahydro-2-methoxy-8,8,10-trimethyl-9-(1-pyrrolidinyl)-pyrido[1,2-a]indole (prepared in Example 15, step 5) (2.81 g, 9 mmol) in chloroform (54 mL) was cooled to 0° C. and treated under dry nitrogen with boron tribromide (5.62 g, 22.5 mmol). The mixture was stirred in the dark at 25° C. for 2 hours. Ethanol (54 mL) was added dropwise over 5 minutes at 0° C. Stirring was continued at 0°-5° C. for 1 hour. Ether (34 mL) was added slowly at 5° C. to induce crystallization. The obtained crystals were filtered, washed with ethanol/ether (2:1) and ether, then dried in vacuo at 65° C. affording 2.24 g (66% yield) of the title compound, m.p. 166°-170° C. as an off-white powder.

Workup

  1. stirringStirring
  2. waitwas continued at 0°-5° C. for 1 hour
  3. customcrystallization
  4. filtrationThe obtained crystals were filtered
  5. washwashed with ethanol/ether (2:1) and ether
  6. customdried in vacuo at 65° C.

Sources & evidence

ORD record
ord-a74d438a797b4adfb8680332ab2b83ac
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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