Methylamine → 1-Benzyloxy-4-(3-methylaminopropoxy)benzene

HRID 2417987Notes

Reaction equation

HRID 2417987 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20]Br)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:2][CH3:1])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 111100311-(Benzyloxy)-4-(3-bromopropoxy)benzene

Product 1

HCID 21991201-Benzyloxy-4-(3-methylaminopropoxy)benzeneYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 150 ml of ethanol containing methylamine (16 g) was added 1-benzyloxy-4-(3-bromopropyloxy)benzene (14 g). The solution was heated for 12 hours at 100° under nitrogen at 1000 psi. The solvent was evaporated in vacuo and the residue treated with 20% sodium hydroxide to ~pH10. The oil was extracted with ethyl acetate and converted in its hydrochloride salt in the usual manner to give 8.4 g (70%) of 1-benzyloxy-4-(3-methylaminopropoxy)benzene as its hydrochloride salt, mp 202°-204.

Workup

  1. temperatureThe solution was heated for 12 hours at 100° under nitrogen at 1000 psi
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue treated with 20% sodium hydroxide to ~pH10
  4. extractionThe oil was extracted with ethyl acetate

Sources & evidence

ORD record
ord-3d7a9a5d51e84a0ebbc95ca0224c544a
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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